Sodium borohydride → HCID 40573861, compound

Participants

Reaction Steps

To a solution of ethyl (2E)-2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate (2500 g, 8.25 mol) in diethyl ether (15 L) under a nitrogen atmosphere was added sodium borohydride (627 g, 16.5 mol) in several batches at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (3×2000 mL). The organic layers were combined, washed with brine (2×500 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether) to afford ethyl N-[(benzyloxy)carbonyl]-3,3,3-trifluoroalaninate.

Provenance & Evidence