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

Participants

Reaction Steps

To a solution of 5.792 g (50.287 mM) of 4-piperidylmethanol in 150 ml of dichloromethane was added 12.1 g (55.3 mM) of di-tert-butyl dicarbonate dropwise at room temperature and the mixture was stirred at the prevailing temperature overnight. The solvent was then distilled off under reduced pressure to recover crude tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate. This crude product was not purified but used as it was in the next reaction. To a solution of the above crude tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate and 18.3 g (55.3 mM) of carbon tetrabromide in 100 ml of acetonitrile was added 14.5 g (55.3 mM) of triphenylphosphine at room temperature and the mixture was stirred at the prevailing temperature for 3 hours. The solvent was then distilled off under reduced pressure. To the residue was added diethyl ether, and after stirring, the resulting precipitate (triphenylphosphine oxide) was filtered off and washed with diethyl ether. The filtrate and washes were combined and concentrated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 15/1 to 9/1) to provide the title compound.

Provenance & Evidence