Sodium borohydride → HCID 59536646, compound

Participants

Reaction Steps

Add sodium borohydride (5.19 g, 145 mmol) portion wise to a solution of (S)-3-butanoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (7.0 g, 29.0 mmol) in methanol (200 mL) and stir at room temperature over night. Add more sodium borohydride (1.4 g, 39 mmol) and stir an hour at room temperature. Evaporate the methanol to half volume, add brine and extract with ethyl acetate. Dry the combine organic phases (MgSO4), filter and concentrate under reduced pressure. Separate the diastereoisomers by silica gel chromatography eluting with 5% isopropylamine in hexanes to provide (3S)-3-(1-hydroxy-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, isomer 1 (S-1) as the first eluting isomer (2.6 g, 37%) and (3S)-3-(1-hydroxy-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, isomer 2 (S-2) as the second eluting isomer (1.8 g, 26%)

Provenance & Evidence