Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Steps

A solution of 1.8 mL (20.4 mMol) oxalyl chloride in 180 mL dichloromethane was cooled to −60° C. at which point 2.9 mL (40.9 mMol) dimethylsulfoxide was added. After stirring for about 5 minutes, a solution of 4.0 gm (18.6 mmol) 1-tert-butoxycarbonyl-4-hydroxymethylpiperidine in dichloromethane was added. After stirring for 20 minutes, 12.9 mL (92.9) mmol triethylamine were added and the resulting solution was allowed to warm to room temperature and was stirred at that temperature for about an hour. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic phase was washed sequentially with 5 N hydrochloric acid and saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure to provide 3.76 gm (95%) of the title compound as a yellow oil.

Provenance & Evidence