3-(4-hydroxyphenyl)propanenitrile

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O·0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O.0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O.0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(4-Hydroxyphenyl)propionitrile (1.47 g, 0.01 mol) was dissolved in DMF (24 ml), and to this solution were successively added benzyl bromide (1.31 ml, 0.011 mol, 1.1 eq) and anhydrous potassium carbonate (4.15 g, 0.030 mol, 3.0 eq). The mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and water (100 ml) was added. The mixture was extracted twice with ethyl acetate (100 ml). The organic layers were combined, washed with saturated brine (200 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(4-benzyloxyphenyl)propionitrile (2.39 g, 100%) as a colorless solid. This reaction mixture was cooled to room temperature The mixture was extracted twice with ethyl acetate (100 ml) washed with saturated brine (200 ml) dried over anhydrous sodium sulfate The drying agent was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O·0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O·0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O.0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title product was prepared from 3-(4-hydroxyphenyl)proprionitrile and N-methyl-N-phenylcarbamoyl chloride. The crude product was subjected to preparative HPLC (11%, colourless oil). HPLC-MS: m/z=281.2 (M+1); Rt: 3.75 min, purity 80%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title product was prepared from 3-(4-hydroxyphenyl)proprionitrile and N-methyl-N-phenylcarbamoyl chloride. The crude product was subjected to preparative HPLC (11%, colourless oil). HPLC-MS: m/z=281.2 (M+1); Rt: 3.75 min, purity 80%.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(4-Hydroxyphenyl)propionitrile (1.47 g, 0.01 mol) was dissolved in DMF (24 ml), and to this solution were successively added benzyl bromide (1.31 ml, 0.011 mol, 1.1 eq) and anhydrous potassium carbonate (4.15 g, 0.030 mol, 3.0 eq). The mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and water (100 ml) was added. The mixture was extracted twice with ethyl acetate (100 ml). The organic layers were combined, washed with saturated brine (200 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(4-benzyloxyphenyl)propionitrile (2.39 g, 100%) as a colorless solid. This reaction mixture was cooled to room temperature The mixture was extracted twice with ethyl acetate (100 ml) washed with saturated brine (200 ml) dried over anhydrous sodium sulfate The drying agent was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O·0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3,3,3-triphenylpropanol (8.70 mmol), 3-(4-hydroxyphenyl)propionitrile (9.40 mmol) and triphenylphosphine (2.42 g, 9.23 mmol) in dry THF (25 mL) under a nitrogen atmosphere at room temperature, was added dropwise DEAD (1.50 mL, 9.52 mmol) in dry THF (20 mL) over approximately 30 minutes. The reaction was heated to reflux overnight. After cooling, the THF was evaporated and the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes. White solid, mp=98°-100° C. (ether), 60% yield. 1H NMR δ 7.18-7.35 (m, 15H), 7.06 (d, J=8.6 Hz, 2H), 6.67 (d, J=8.6 Hz, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.13 (t, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 2.54 (t, J=7.3 Hz, 2H). IR 2243, 1540 cm-1. MS 418 (MH+), 243. Anal. calcd. for C30H27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.07; H, 6.39; N, 3.24. To a solution of trimethyl aluminum (1M in hexanes, 0.57 mL), in toluene (3 mL) at ~2° C., was added azidotrimethylsilane (0.569 mmol). A solution of nitrile (0.474 mmol) in toluene (2 mL) was slowly added. The reaction was stirred at 80° C. for 72 h. The cooled (0° C.) reaction was added dropwise to HCl (6M, 10 mL) and EtOAc (10 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The crude material was triturated with dichloromethane to remove unreacted starting nitrile leaving behind the title compound as a hydrate, a white solid (mp=193°-195° C., 30% yield). 1H NMR (DMSO-d6) δ 7.19-7.35 (m, 15H), 7.02 (d, J=8.5 Hz, 2H), 6.58 (d, J=8.5 Hz, 2H), 3.60 (t, J=7.4 Hz, 2H), 3.04-3.12 (m, 4H), 2.91 (t, J=7.6 Hz, 2H). IR 3300-3450 (br), 1586, 1511 cm-1. MS 461 (MH+), 243. Anal. calcd. for C30H28N4O.0.25H2O: C, 77.48; H, 6.18; N, 12.05. Found: C, 77.18; H, 5.96; N, 11.71. The reaction was heated to reflux overnight After cooling the THF was evaporated the residue chromatographed on a silica column, with 15-20% EtOAc/hexanes The cooled (0° C.) reaction The resulting mixture was extracted with EtOAc (2×50 mL) The combined organic layers were dried (MgSO4) filtered evaporated The crude material was triturated with dichloromethane to remove unreacted