Carbon tetrabromide → tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (8.75 g, 40.64 mmol) in diethyl ether (200 mL) at 0° C. under nitrogen. were added triphenyl phosphine (21.32 g, 81.28 mmol) and carbon tetrabromide (26.96 g, 81.28 mmol). The mixture was allowed to warm to room temperature and stirred under nitrogen for 48 h. The reaction mixture was filtered through a pad of Celite and the organic filtrate was washed with 5% NaS2O3, water, brine, and dried. The mixture was filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (ethyl acetate/hexane, 1:9) to give 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (8.26 g, 73%).

Provenance & Evidence