Ethanol → 1,1-Dimethylethyl N-[(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (0.47 g, 1.8 mmol) in THF (4.0 mL) at −10° C., NaBH4 (0.207 g, 5.48 mmol) was added followed by EtOH (1.0 mL). After stirring at −10° C. for 1 h, the mixture was allowed to warm to room temperature and stirred for 15 h. The reaction mixture was then diluted with EtOAc (50 mL), washed with water (25 mL) and brine (30 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product (0.39 g, 92%) was used directly in the next step without further purification. LCMS calc. for C11H24NO4 (M+H)+: m/z=234.2. found no ionization.

Provenance & Evidence