Dimethyl Sulfoxide → HCID 86693765, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (6.28 mL, 72.4 mmol) in dichloromethane (75 mL) at −60° C. under nitrogen is added a solution of DMSO (10.7 mL, 151 mmol) in dichloromethane (75 mL) dropwise and stirred at −60° C. for 15 min. (1R,2S)-2-(dibenzylamino)cyclopentanol (17.0 g, 60 mmol) in dichloromethane (75 mL) is added and the reaction is stirred at −60° C. for 30 min. TEA (46 mL, 330 mmol) is added and the reaction is allowed to warm to room temperature and stirred for 1 h. Water is added (100 mL) and the reaction is stirred overnight. The dichloromethane layer is separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (13.96 g, 83%). ES/MS m/z 280 (M+1).

Provenance & Evidence