5-(dibenzylamino)-2-methylpentan-2-ol

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

Procedure: Add diethylaminosulfur trifluoride (17.9 g, 111 mmol) drop-wise to a −78° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (11 g, 37 mmol) in DCM (100 mL), under N2, warm to RT and stir overnight. Pour the mixture into ice-water, neutralize with satd. NaHCO3, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (4.5 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 7.30-7.13 (m, 10H), 3.48 (s, 4H), 2.35 (m, 2H), 1.51-1.48 (m, 4H), 1.22 (d, J=21.2 Hz, 6H). NaHCO3, extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treat a 0° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (3 g, 10.2 mmol) in THF (25 mL), under N2, portion-wise with KH (30%, 1.5 g, 11.3 mmol), stir at 0° C. for 0.5 h, add MeI (1.6 g, 11.3 mmol) drop-wise, warm to RT and stir for 3 h. Cool to 0° C., quench with satd. NH4Cl, partially concentrate under reduced pressure, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (3.1 g, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.21 (m, 10H), 3.57 (s, 4H), 3.14 (s, 3H), 2.42 (t, J=7.2 Hz, 2H), 1.58-1.52 (m, 2H), 1.43-1.39 (m, 2H), 1.11 (s, 6H). warm to RT stir for 3 h Cool to 0° C. quench with satd NH4Cl, partially concentrate under reduced pressure extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treat a 0° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (3 g, 10.2 mmol) in THF (25 mL), under N2, portion-wise with KH (30%, 1.5 g, 11.3 mmol), stir at 0° C. for 0.5 h, add MeI (1.6 g, 11.3 mmol) drop-wise, warm to RT and stir for 3 h. Cool to 0° C., quench with satd. NH4Cl, partially concentrate under reduced pressure, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (3.1 g, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.21 (m, 10H), 3.57 (s, 4H), 3.14 (s, 3H), 2.42 (t, J=7.2 Hz, 2H), 1.58-1.52 (m, 2H), 1.43-1.39 (m, 2H), 1.11 (s, 6H). warm to RT stir for 3 h Cool to 0° C. quench with satd NH4Cl, partially concentrate under reduced pressure extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography

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

Procedure: Add diethylaminosulfur trifluoride (17.9 g, 111 mmol) drop-wise to a −78° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (11 g, 37 mmol) in DCM (100 mL), under N2, warm to RT and stir overnight. Pour the mixture into ice-water, neutralize with satd. NaHCO3, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (4.5 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 7.30-7.13 (m, 10H), 3.48 (s, 4H), 2.35 (m, 2H), 1.51-1.48 (m, 4H), 1.22 (d, J=21.2 Hz, 6H). NaHCO3, extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treat a 0° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (3 g, 10.2 mmol) in THF (25 mL), under N2, portion-wise with KH (30%, 1.5 g, 11.3 mmol), stir at 0° C. for 0.5 h, add MeI (1.6 g, 11.3 mmol) drop-wise, warm to RT and stir for 3 h. Cool to 0° C., quench with satd. NH4Cl, partially concentrate under reduced pressure, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (3.1 g, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.21 (m, 10H), 3.57 (s, 4H), 3.14 (s, 3H), 2.42 (t, J=7.2 Hz, 2H), 1.58-1.52 (m, 2H), 1.43-1.39 (m, 2H), 1.11 (s, 6H). warm to RT stir for 3 h Cool to 0° C. quench with satd NH4Cl, partially concentrate under reduced pressure extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography