Dimethyl Sulfoxide → tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Participants

Reaction Steps

To a mixture of DMSO (53 g, 0.68 mol) and oxalylchloride (43 g, 0.34 mol) in dry dichloromethane (1.51) at −78° C. was added tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)pyrrolidine-1-carboxylate (75 g, 0.226 mol) drop-wise. After stiring at −78° C. for 1 h, was added triethylamine (158 ml, 1.13 mol) drop-wise and warmed the reaction mixture slowly to RT. The reaction mixture was diluted with water and separated the organic layer. The organic layer was washed with brine and dried. The solvent was removed under vacuum to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate (70 g) as pale yellow liquid. Yield: 94%

Provenance & Evidence