1-amino-4-methylpentan-2-ol

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

Procedure: 2,3-Dichloroquinoxaline (18.05 g, 90.7 mmol) is added to a solution of crude 1a (11.7 g, 99.8 mmol) and Et3N (19 ml, 13.8 g, 136 mmol) in dioxane (210 ml). The solution obtained is heated at reflux (under N2) for 6 h, it is then cooled to room temperature. Et3N, HCl is eliminated by filtration and the filtrate is concentrated under reduced pressure. The dark orange residue is purified by chromatography on a silica column, eluent: CH2Cl2/MeOH (100:0→99:1), to obtain a yellow solid (12.14 g, 48%); 1H NMR (100 MHz, CDCl3) δ: 0.72 (d, 3H), 0.78 (d, 3H), 1.60 (m, 3H), 3.68 (m, 4H), 5.82 (t, 1H), 7.58 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.17, 23.35, 24.60, 44.32, 48.62, 69.67, 125.30, 125.62, 127.91, 130.36, 136.52, 137.92, 140.59, 148.62. Analysis calculated for C14H18N3OCl: C, 60.10; H, 6.49; N, 15.02. Experimental: C, 59.87; H, 6.62; N, 15.25. The solution obtained is heated Et3N, HCl is eliminated by filtration the filtrate is concentrated under reduced pressure The dark orange residue is purified by chromatography on a silica column, eluent

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

Procedure: 1b is prepared from 2-hydroxy-4-phenylbutanenitrile according to the protocol described for 1a; LiAlH4 (6.2 g, 163 mmol), Et2O (120 ml), 2-hydroxy-4-phenylbutanenitrile (12.4 g, 77 mmol), H2O (6.2 ml), 15% aqueous NaOH (6.2 ml) and H2O (18 ml). The product, an orange oil, is used with no other purification (11 g, 87%); 1H NMR (100 MHz, CDCl3) δ: 1.80 (m, 3H), 2.65 (m, 4H), 3.62 (m, 3H), 7.21 (s, 5H); 13C NMR (25 MHz, CDCl3) δ: 33.98, 36.25, 70.92, 125.46, 128.04, 141.74. Analysis calculated for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Experimental: C, 72.45; H, 9.33; N, 8.24. The product, an orange oil, is used with no other purification (11 g, 87%)

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

Procedure: 2,3-Dichloroquinoxaline (18.05 g, 90.7 mmol) is added to a solution of crude 1a (11.7 g, 99.8 mmol) and Et3N (19 ml, 13.8 g, 136 mmol) in dioxane (210 ml). The solution obtained is heated at reflux (under N2) for 6 h, it is then cooled to room temperature. Et3N, HCl is eliminated by filtration and the filtrate is concentrated under reduced pressure. The dark orange residue is purified by chromatography on a silica column, eluent: CH2Cl2/MeOH (100:0→99:1), to obtain a yellow solid (12.14 g, 48%); 1H NMR (100 MHz, CDCl3) δ: 0.72 (d, 3H), 0.78 (d, 3H), 1.60 (m, 3H), 3.68 (m, 4H), 5.82 (t, 1H), 7.58 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.17, 23.35, 24.60, 44.32, 48.62, 69.67, 125.30, 125.62, 127.91, 130.36, 136.52, 137.92, 140.59, 148.62. Analysis calculated for C14H18N3OCl: C, 60.10; H, 6.49; N, 15.02. Experimental: C, 59.87; H, 6.62; N, 15.25. The solution obtained is heated Et3N, HCl is eliminated by filtration the filtrate is concentrated under reduced pressure The dark orange residue is purified by chromatography on a silica column, eluent

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

Procedure: 2,3-Dichloroquinoxaline (18.05 g, 90.7 mmol) is added to a solution of crude 1a (11.7 g, 99.8 mmol) and Et3N (19 ml, 13.8 g, 136 mmol) in dioxane (210 ml). The solution obtained is heated at reflux (under N2) for 6 h, it is then cooled to room temperature. Et3N, HCl is eliminated by filtration and the filtrate is concentrated under reduced pressure. The dark orange residue is purified by chromatography on a silica column, eluent: CH2Cl2/MeOH (100:0→99:1), to obtain a yellow solid (12.14 g, 48%); 1H NMR (100 MHz, CDCl3) δ: 0.72 (d, 3H), 0.78 (d, 3H), 1.60 (m, 3H), 3.68 (m, 4H), 5.82 (t, 1H), 7.58 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.17, 23.35, 24.60, 44.32, 48.62, 69.67, 125.30, 125.62, 127.91, 130.36, 136.52, 137.92, 140.59, 148.62. Analysis calculated for C14H18N3OCl: C, 60.10; H, 6.49; N, 15.02. Experimental: C, 59.87; H, 6.62; N, 15.25. The solution obtained is heated Et3N, HCl is eliminated by filtration the filtrate is concentrated under reduced pressure The dark orange residue is purified by chromatography on a silica column, eluent

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

Procedure: 1b is prepared from 2-hydroxy-4-phenylbutanenitrile according to the protocol described for 1a; LiAlH4 (6.2 g, 163 mmol), Et2O (120 ml), 2-hydroxy-4-phenylbutanenitrile (12.4 g, 77 mmol), H2O (6.2 ml), 15% aqueous NaOH (6.2 ml) and H2O (18 ml). The product, an orange oil, is used with no other purification (11 g, 87%); 1H NMR (100 MHz, CDCl3) δ: 1.80 (m, 3H), 2.65 (m, 4H), 3.62 (m, 3H), 7.21 (s, 5H); 13C NMR (25 MHz, CDCl3) δ: 33.98, 36.25, 70.92, 125.46, 128.04, 141.74. Analysis calculated for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Experimental: C, 72.45; H, 9.33; N, 8.24. The product, an orange oil, is used with no other purification (11 g, 87%)

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

Procedure: 2,3-Dichloroquinoxaline (18.05 g, 90.7 mmol) is added to a solution of crude 1a (11.7 g, 99.8 mmol) and Et3N (19 ml, 13.8 g, 136 mmol) in dioxane (210 ml). The solution obtained is heated at reflux (under N2) for 6 h, it is then cooled to room temperature. Et3N, HCl is eliminated by filtration and the filtrate is concentrated under reduced pressure. The dark orange residue is purified by chromatography on a silica column, eluent: CH2Cl2/MeOH (100:0→99:1), to obtain a yellow solid (12.14 g, 48%); 1H NMR (100 MHz, CDCl3) δ: 0.72 (d, 3H), 0.78 (d, 3H), 1.60 (m, 3H), 3.68 (m, 4H), 5.82 (t, 1H), 7.58 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.17, 23.35, 24.60, 44.32, 48.62, 69.67, 125.30, 125.62, 127.91, 130.36, 136.52, 137.92, 140.59, 148.62. Analysis calculated for C14H18N3OCl: C, 60.10; H, 6.49; N, 15.02. Experimental: C, 59.87; H, 6.62; N, 15.25. The solution obtained is heated Et3N, HCl is eliminated by filtration the filtrate is concentrated under reduced pressure The dark orange residue is purified by chromatography on a silica column, eluent

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

Procedure: 1b is prepared from 2-hydroxy-4-phenylbutanenitrile according to the protocol described for 1a; LiAlH4 (6.2 g, 163 mmol), Et2O (120 ml), 2-hydroxy-4-phenylbutanenitrile (12.4 g, 77 mmol), H2O (6.2 ml), 15% aqueous NaOH (6.2 ml) and H2O (18 ml). The product, an orange oil, is used with no other purification (11 g, 87%); 1H NMR (100 MHz, CDCl3) δ: 1.80 (m, 3H), 2.65 (m, 4H), 3.62 (m, 3H), 7.21 (s, 5H); 13C NMR (25 MHz, CDCl3) δ: 33.98, 36.25, 70.92, 125.46, 128.04, 141.74. Analysis calculated for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Experimental: C, 72.45; H, 9.33; N, 8.24. The product, an orange oil, is used with no other purification (11 g, 87%)