1-N-Boc-4-Piperidinecarboxylic acid methyl ester → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

LAH (3.8 g, 100 mmol) was added portionwise to a solution the ester 2-3c (20.3 g, 83.5 mmol) in THF (300 mL) at 0° C. under argon. After the addition was complete, the mixture was stirred for 2 hours then poured onto ice, IN HCl was added and the slurry extracted 3× EtOAc. The organic layer was washed with water then brine, dried (MgSO4) and concentrated to give a white solid. The solid was swished with hexane/ether 9:1 and filtered to provide the alcohol 2-3.

Provenance & Evidence