tert-Butyl 2-oxopiperidine-1-carboxylate → 1-Boc-4-Methylenepiperidine

Participants

Reaction Steps

To a solution of methyl triphenylphosphonium bromide (5.4 g, 15.05 mmol) in THF (100 mL) was added slowly butyl lithium (2M, 15.05 mmol) at −78° C. The mixture was allowed to stir for one hour and N-Boc-piperidinone (2 g, 10.03 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The THF was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulphate, filtered and concentrated. The compound was purified by column chromatography (30% Hexanes/EtOAc) to provide the title compound (1.96 g, 99%).

Provenance & Evidence