Water → (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol

Participants

Reaction Conditions

Reaction Steps

Borane-dimethyl sulfide (0.63 ml, 6.3 mmol) was added to a solution of (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylcarboxylic acid (1.12 g, 3.13 mmol) in THF (30 ml) under stirring at 0° C. The reaction mixture was stirred at 50° C. for 1.5 hours. After the reaction mixture was cooled to 0° C., water (20 ml) was added thereto. The mixture was then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (50/1) eluate fractions, the title compound (1.10 g, 100%) was obtained as a pale yellow oil.

Provenance & Evidence