Dimethyl Sulfoxide → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Participants

Reaction Steps

Oxalyl chloride (3.2 mL, 0.04 mol) and dimethyl sulfoxide (4.3 mL, 0.06 mol) were dissolved in 100 mL of dichloromethane in a dry ice bath. After stirring for 30 minutes, a solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 2b (2 g, 0.01 mol) in 20 mL of dichloromethane was added dropwise. The reaction mixture was stirred for 45 minutes, and triethylamine (7.08 g, 0.07 mol) was added dropwise. After stirring for another 1 hours at 0° C., the reaction mixture was added with 500 mL of dichloromethane. The combined organic layers were washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound tert-butyl(2S)-2-formylpyrrolidine-1-carboxylate 2c (1.10 g, yield 55.4%) as a light yellow oil.

Provenance & Evidence