tert-butyl N-[(1S)-2-oxo-1-phenylpropyl]carbamate

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

Procedure: At 0° C., to a solution of ((S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate (0.7 g, 2.8 mmol) in MeOH (10 mL) was added NaBH4 (0.1 g, 2.8 mmol) and the contents were stirred at ambient temperature. After 30 min, the reaction mixture was quenched carefully with ice cold H2O (10 mL), and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated to afford tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate. The product thus obtained was pure and taken directly for the next step without further purification. MS: [M+H-Boc]+ m/z 152. the reaction mixture was quenched carefully with ice cold H2O (10 mL) the organic contents were extracted with EtOAc (3×25 mL) The combined organic extracts were washed with brine (1×20 mL) dried over Na2SO4 concentrated

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

Procedure: At 0° C., to a solution of ((S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate (0.7 g, 2.8 mmol) in MeOH (10 mL) was added NaBH4 (0.1 g, 2.8 mmol) and the contents were stirred at ambient temperature. After 30 min, the reaction mixture was quenched carefully with ice cold H2O (10 mL), and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated to afford tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate. The product thus obtained was pure and taken directly for the next step without further purification. MS: [M+H-Boc]+ m/z 152. the reaction mixture was quenched carefully with ice cold H2O (10 mL) the organic contents were extracted with EtOAc (3×25 mL) The combined organic extracts were washed with brine (1×20 mL) dried over Na2SO4 concentrated

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

Procedure: At 0° C., to a solution of (S)-tert-butyl(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate (0.9 g, 3.06 mmol) in anhydrous THF (15 mL), was added MeMgBr (3M solution in Et2O, 2.0 mL, 6.1 mmol) and resultant mixture was allowed to warm and stirred at ambient temperature. After 2 hrs, the reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL), and the organic contents were extracted with CH2Cl2 (3×25 mL). The volatiles were removed under reduced pressure to afford (S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate. The compound obtained is pure and no further purification is necessary. 1H NMR (300 MHz, CDCl3) δ 7.40-7.33 (m, 5H), 5.88 (bs, 1H), 5.28 (bs, 1H), 2.08 (s, 3H), 1.41 (s, 9H). to warm the reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL) the organic contents were extracted with CH2Cl2 (3×25 mL) The volatiles were removed under reduced pressure

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

Procedure: At 0° C., to a solution of ((S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate (0.7 g, 2.8 mmol) in MeOH (10 mL) was added NaBH4 (0.1 g, 2.8 mmol) and the contents were stirred at ambient temperature. After 30 min, the reaction mixture was quenched carefully with ice cold H2O (10 mL), and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated to afford tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate. The product thus obtained was pure and taken directly for the next step without further purification. MS: [M+H-Boc]+ m/z 152. the reaction mixture was quenched carefully with ice cold H2O (10 mL) the organic contents were extracted with EtOAc (3×25 mL) The combined organic extracts were washed with brine (1×20 mL) dried over Na2SO4 concentrated

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

Procedure: At 0° C., to a solution of (S)-tert-butyl(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate (0.9 g, 3.06 mmol) in anhydrous THF (15 mL), was added MeMgBr (3M solution in Et2O, 2.0 mL, 6.1 mmol) and resultant mixture was allowed to warm and stirred at ambient temperature. After 2 hrs, the reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL), and the organic contents were extracted with CH2Cl2 (3×25 mL). The volatiles were removed under reduced pressure to afford (S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate. The compound obtained is pure and no further purification is necessary. 1H NMR (300 MHz, CDCl3) δ 7.40-7.33 (m, 5H), 5.88 (bs, 1H), 5.28 (bs, 1H), 2.08 (s, 3H), 1.41 (s, 9H). to warm the reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL) the organic contents were extracted with CH2Cl2 (3×25 mL) The volatiles were removed under reduced pressure