Hydrochloric Acid → benzyl N-[(3R)-3,4-dihydroxybutyl]carbamate

Participants

Reaction Steps

A solution of (R)-4-benzyloxycarbonylamino-2-hydroxy-butyric acid ethyl ester (2.17 g, 7.71 mmol) in EtOH (6 mL) was added dropwise at <15° C. to a suspension of sodium borohydride (583 mg, 15.4 mmol) in EtOH (4 mL). The reaction mixture was stirred at RT for 16 h, then cooled to 5° C. and treated with MeOH (3 mL), then after 30 min acidified to pH 1-2 with conc. aq. HCl solution. The reaction mixture was stirred for 1 h, then diluted with CH2Cl2, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2/MeOH gradient) afforded the title compound (1.76 g, 96%). Light yellow solid, MS: 262.1 (M+Na)+.

Provenance & Evidence