Sodium borohydride → HCID 23237021, compound

Participants

Reaction Steps

To a suspension of calcium chloride (2885 g, 26.23 mol) in diethyl ether (8 L) under a nitrogen atmosphere was added sodium borohydride (1993 g, 52.45 mol). To this mixture was added dropwise ethyl N-[(benzyloxy)carbonyl]-3,3,3-trifluoroalaninate (3.28 M solution in diethyl ether, 2000 mL, 6.56 mol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, reaction mixture was quenched with water (10 L) 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 benzyl (1,1,1-trifluoro-3-hydroxypropan-2-yl)carbamate.

Provenance & Evidence