Dimethyl Sulfoxide → HCID 86638697, compound

Participants

Reaction Steps

To a solution of 0.3 mL of oxalyl chloride in 5 mL of dichloromethane was added dropwise 0.5 mL of DMSO at −78° C., followed by stirring for 10 minutes. To the reaction mixture was added dropwise a solution of 664 mg of 4-(methoxycarbonyl)phenyl rel-(3R,4S)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate in 5 mL of dichloromethane at −78° C., followed by stirring for 15 min, and a solution of 1.8 mL of diisopropylethylamine in 3 mL of dichloromethane was then added dropwise, followed by elevation to room temperature over 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diethylether, followed by washing with saturated brine, and drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 4-(methoxycarbonyl)phenyl rel-(3R,4S)-4-(4-fluorophenyl)-3-formylpiperidine-1-carboxylate as a crude product. ESI+: 386

Provenance & Evidence