Dimethyl Sulfoxide → HCID 86638698, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of 1.62 mL of DMSO in 40 mL of dichloromethane cooled in a dry ice-acetone bath was added dropwise 0.996 mL of oxalyl chloride, while keeping the inner temperature at −70° C. or lower. After stirring for 10 minutes, a solution of 1.64 g of rel-[(3R,4R)-3-phenyl-1-(trifluoroacetyl)piperidin-4-yl]methanol in 25 mL of dichloromethane was added dropwise thereto over 20 minutes. After stirring over 10 min while keeping it at −70° C. or lower, 4.77 mL of triethylamine was added dropwise thereto over 15 min, and the reaction system was warmed to −30° C., followed by stirring for 15 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by warming to room temperature. After extraction with chloroform, the organic layer was washed with water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain rel-(3R,4R)-3-phenyl-1-(trifluoroacetyl)piperidine-4-carbaldehyde as a crude product (as a pale yellow oily substance, 1.78 g).

Provenance & Evidence