Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

Participants

Reaction Steps

A solution containing 4-piperidinol (5 g) and triethylamine (7 ml) in dichloromethane (50 ml) was treated with benzyl chloroformate (7.5 ml), added dropwise, and the resulting mixture was allowed to stand for 2 hours. The mixture was diluted with dichloromethane (50 ml) and washed with water (2×50 ml) and with saturated brine (50 ml). The organic solution was dried (MgSO4) and concentrated. The residue was purified by column chromatography, eluting with ether/hexane (50%, then 75%) followed by ether, to give 1-(benzyloxycarbonyl)piperidin-4-ol (7.5 g) as a colourless oil; NMR Spectrum 1.2-1.4 (2H, m); 1.6-1.8 (2H, m); 3.0-3.2 (2H, m); 3.6-3.8 (3H, m); 4.7 (1H, d); 5.05 (2H, s); 7.3-7.4 (5H, m).

Provenance & Evidence