Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

Participants

Reaction Steps

An ice-cooled solution containing 4-piperidinol (5 g, 50 mMoles) and triethylamine (7 ml, 50 mMoles) in dichloromethane (50 ml) was cautiously treated with benzylchloroformate (7.5 ml, 50 mMoles) and allowed to stir for 2 hours. Dichloromethane (25 ml) was added and the solution was washed sequentially with water (2×40 ml) and saturated brine (50 ml), then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by vacuum flash chromatography, eluting with a gradient of 50-100% ether in hexane to give N-benzyloxycarbonyl piperidin-4-ol (7.5 g) as a colourless oil; NMR (d6DMSO): 1.2-1.4 (m,2H), 1.6-1.8 (m,2H), 3.0-3.2 (m,2H), 3.6-3.8 (m,3H), 4.7 (d,2H), 5.1 (2,2H), 7.3 (m,5H); m/e 236 (M+H)+.

Provenance & Evidence