Sodium borohydride → tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate

Participants

Reaction Steps

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.

Provenance & Evidence