Dimethyl Sulfoxide → (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A 0.43 ml portion of DMSO was dissolved in 6 ml of dichloromethane, and a 3 ml dichloromethane solution of 0.26 ml of oxalyl chloride was added thereto while keeping the internal temperature at −60° C. or less. After 30 minutes of stirring, a 10 ml dichloromethane solution of 270 mg of [(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]methanol which had been synthesized in accordance with the technique of Ling et al. (“Tetrahedron”, 2001, vol. 57, p. 6579-6588) and the method of International Patent Publication WO 2000/59502 was added thereto while keeping the internal temperature at −60° C. or less and stirred for 30 minutes. A 1.27 ml portion of triethylamine was added to the reaction solution while keeping the internal temperature at −50° C. or less, and then the internal temperature was allowed to warm to 0° C. over 30 minutes or more, and this was stirred at 0° C. for 30 minutes. The reaction solution was mixed with water to quench the reaction and extracted with chloroform. The organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure to obtain (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carboaldehyde as a crude product.

Provenance & Evidence