Dimethyl Sulfoxide → HCID 58055030, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.51 mL) in CH2Cl2 (7.3 mL) was added a 4.0M CH2Cl2 solution of DMSO (0.86 mL) at −78° C. After 10 min, a solution of tert-butyl (3S,4S)-3-hydroxy-4-(tert-butyldimethylsilyl)oxypyrrolidine-1-carboxylate (920 mg) in CH2Cl2 (5.8 mL) was added, and the mixture was stirred for 2 hours at −45° C. Triethylamine (3.25 mL) was added, and after being stirred for 10 min at room temperature, water was added. The mixture was separated, and the aqueous layer was extracted with ether. The combined organic layer was washed with brine, and dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50) to give tert-butyl (3S)-3-(tert-butyldimethylsilyl)oxy-4-oxopyrrolidine-1-carboxylate as a pale yellow foam.

Provenance & Evidence