Carbon tetrabromide → HCID 21994134, compound

Participants

Reaction Steps

To a solution of 15.292 g (67.277 mM) of tert-butyl 4-(2-hydroxyethylidene)piperidine-1-carboxylate and 24.5 g (74.0 mM) of carbon tetrabromide in 150 ml of acetonitrile was added 19.4 g (74.0 mM) of triphenylphosphine at −78° C. Then, at room temperature, the mixture was stirred for 2 hours. This reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added diethyl ether, followed by stirring, and the resulting precipitate was filtered off and washed with diethyl ether. The filtrate and washes were pooled and the solvent was distilled under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 9/1) to provide the title compound.

Provenance & Evidence