Methanol → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 250-mL 3-necked round-bottomed flask was charged with a solution of LiAlH4 (2.96 g, 77.83 mmol, 2.00 equiv) in THF (150 mL). To this solution was added 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (11.4 g, 39.16 mmol, 1.00 equiv) in THF (50 mL) drop wise with stirring at −10° C. The resulting mixture was allowed to stir about 1 hour at −10° C. The progress was monitored by TLC (DCM: MeOH=10:1). The resulting solution was diluted with 10 mL of NaOH/H2O. The solids were filtered out. The resulting mixture was concentrated on a rotary evaporator to afford benzyl 3-(hydroxymethyl)piperidine-1-carboxylate as pale yellow oil in (8.94 g, (92%).

Provenance & Evidence