Acetic Acid → HCID 124518668, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-benzyl 3-oxocyclopentanecarboxylate (2 g, 9.16 mmol) in methanol (40 ml) was added sodium borohydride (0.35 g, 9.16 mmol) in portion wise manner at 0° C. and the reaction was allowed to stir at 0° C. for 20 min. Upon completion, acetic acid (0.57 ml, 10.08 mmol) was added to the reaction mixture and stirring was continued for 5 min. Methanol was removed under reduced pressure and to the residue was added water (50 ml). The organic mass was extracted using ethyl acetate (2×50 ml). Combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain a crude compound, which was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain (1S)-benzyl 3-hydroxycyclopentanecarboxylate as a diastereomeric mixture (75:25) of title compound (1.6 g, 79%).

Provenance & Evidence