Water → 1-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

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Reaction Steps

Triethylamine (14.8 ml, 106.0 mM) and methanesulfonyl chloride (6.9 ml, 90.0 mM) were added to a solution of methyl (2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (20 g, 81.5 mM) in anhydrous tetrahydrofuran (200 ml) under ice-cooling in a nitrogen gas stream, and the mixture was stirred for 30 minutes. The reaction mixture was poured into water followed by extracting with ethyl acetate, the organic layer was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate and the solvent was removed to give the title compound almost quantitatively (27 g).

Provenance & Evidence