Chloroacetic Acid → HCID 86757492, compound

Participants

Reaction Steps

To a solution of 0.242 g (0.75 mmol) of 1-butyloxycarbonyl (trans)-3-hydroxy4-(3-phenylpropyl)piperidine, 0.189 g (1.5 mmol) of chloroacetic acid, and 0.524 g (1.5 mmol) of triphenylphosphine in 5 mL of THF at 0° C. was slowly added 0.348 g (1.5 mmol) of diethylazodicarboxylate (DEAD). The reaction mixture was allowed to warm to rt and was stirred for 16 h. To the reaction mixture was added 20 mL of ether and it was filtered through a thin pad of celite. The filtrate was washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1) to give the title compound.

Provenance & Evidence