Dimethyl Sulfoxide → 1,1-Dimethylethyl (2S,4R)-2-formyl-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate

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Reaction Steps

A solution of dimethyl sulfoxide (4.2 ml, 59.3 mM) in anhydrous methylene chloride(20 ml) was added dropwise into a solution of oxalyl chloride (3.5 ml, 40.3 mM) in anhydrous methylene chloride (100 ml) at −70 ° C. in a nitrogen gas stream and the mixture was stirred for 20 minutes. A solution of (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxy-2-hydorxymethylpyrrolidine (7 g, 23.7 mM) in anhydrous methylene chloride (20 ml) was added dropwise and the mixture was further stirred for 20 minutes. After adding dropwise triethylamine (11.6 ml, 83.0 mM) thereto, the mixture was warmed up to room temperature. The reaction mixture was poured into water and the organic layer was washed with a 10% aqueous solution of citric acid, water, a saturated aqueous solution of sodium carbonate and brine in this order and dried over anhydrous magnesium sulfate. After removing the solvent, the resulting solid matter was washed with hexane to give the title compound (6.5 g, 93%).

Provenance & Evidence