Sodium borohydride → benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl (2R)-2-methyl-5-oxopiperidine-1-carboxylate (365 mg, 1.47 mmol) in methanol (2.9 mL) at 0° C. was added sodium borohydride (84 mg, 2.21 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then stirred for 16 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was extracted with DCM (3×) and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate. MS ESI calc'd. for C14H19NO3 [M+H]+ 250. found 250.

Provenance & Evidence