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

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To a solution of 1 ml (14.1 mmol) of DMSO in 7 ml of dichloromethane were added 1.48 ml (10.4 mmol) of trifluoroacetic anhydride in 3.5 ml of dichloromethane at −78° C. under a slight stream of argon. After 10 min, 2.35 g (7 mmol) of (2S,4R)-1-Boc-4-[t-butyldimethylsilyloxy]-2-(hydroxymethyl)pyrrolidine, prepared as in Example 171A, in 7 ml of dichloromethane was added to this mixture at the same temperature. The reaction mixture was stirred for 1 hour. To this solution was added 3 ml (21.5 mmol) of triethylamine. The reaction mixture was stirred for 1 hour at −78° C., slowly warmed to room temperature, and concentrated. The residue was chromatographed on silica gel (9:1 hexanes-ethyl acetate to yield 1.08 g (47%) of (2S,4R)-1-Boc-4-[t-butyldimethylsilyloxy]-pyrrolidin-2-aldehyde as an oil:

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