Water → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A 1M-borane/tetrahydrofuran solution (4.36 ml, 4.36 mmol) was added dropwise to a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1.0 g, 4.36 mmol) in tetrahydrofuran (20 ml) at 0° C. After 1 hour, the mixture thus obtained was warmed up to room temperature. After another 6 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture and the resulting mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (715 mg, 76%).

Provenance & Evidence