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

Participants

Reaction Steps

A solution of methyltriphenylphosphonium bromide (2.15 g, 6.02 mmol) in hexane (15 mL) was added with tert-butoxypotassium (0.676 g, 6.02 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added portionwise with tert-butyl 4-oxopiperidine-1-carboxylate (1.10 g, 5.52 mmol), and the mixture was stirred overnight at room temperature. The solid was removed by filtration, the concentrated filtrate was added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-methylenepiperidine-1-carboxylate (0.731 g, 67%).

Provenance & Evidence