Dimethyl Sulfoxide → HCID 86638695, compound

Participants

Reaction Steps

A solution of 1.37 mL of DMSO in 20 mL of dichloromethane was cooled to −78° C., and added dropwise 0.845 mL of oxalyl chloride (internal temperature −60° C. or lower). After stirring at the same temperature for 20 minutes, a solution of 1.46 g of rel-[(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidin-3-yl]methanol in 20 mL of dichloromethane was added dropwise thereto, followed by stirring for additional 20 minutes. 4.40 mL of triethylamine was added dropwise thereto, and the reaction temperature was then elevated to −30° C., followed by stirring for additional 15 minutes. To the reaction mixture was added a saturated ammonium chloride solution to stop the reaction, followed by warming to room temperature, and then extraction with chloroform. The organic layer was washed with water, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 1.597 g of rel-(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidine-3-carbaldehyde as a crude product.

Provenance & Evidence