Sodium borohydride → HCID 58530016, compound

Participants

Reaction Conditions

Reaction Steps

A solution of allyl (4R)-4-[(benzyloxy)amino]-1-(trifluoroacetyl)-L-prolinate (1.19 g, 3.20 mmol) in methanol (9.5 mL) was added slowly to a solution of sodium borohydride (312 mg, 8.25 mmol) in methanol (9.5 mL) at −10° C. The reaction mixture was allowed to warm to 0° C. slowly then stirred at 0° C. for 3 hours. Additional sodium borohydride (0.29 g, 7.67 mmol) was added at 0° C. and the reaction mixture was stirred at 0° C. for three hours then silica gel (to pre-absorb the crude product for chromatography) was added and the solvent removed under vacuum. The residue was chromatographed on silica gel eluted with 15:9:1 dichloromethane:ethyl acetate:methanol to afford the title compound as a colorless oil.

Provenance & Evidence