Dimethyl Sulfoxide → 1-Tritylpiperidin-3-one

Participants

Reaction Steps

To a solution of 1.7 mL (24 mmol) of DMSO in 30 mL of dichloromethane at −50° C. was added dropwise 5.5 mL (11.0 mmol) of 2.0 M oxalyl chloride solution in dichloromethane. After 10 min, a solution of 3.85 g (10.0 mmol) of 3-hydroxy-1-(triphenylmethyl)piperidine from Step A in 15 mL of dichloromethane was added dropwise. After 15 min, 7.0 mL (50 mmol) of triethylamine was added dropwise. The reaction mixture was allowed to warm to ambient temperature over 0.5 h. The mixture was diluted with dichloromethane, washed sequentially with water, 5% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography (silica gel, 6% ethyl acetate/hexane) gave 1.95 g (57%) of the title compound as a white crystalline solid.

Provenance & Evidence