p-Bromobenzenesulfonyl chloride → 1-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

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Reaction Steps

To a solution of 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.15 g, 8.76 mmol) and DABCO (1.57 g, 14.0 mmol) in PhMe (10 mL) at RT was added a solution of brosyl chloride (3.14 g, 12.3 mmol) in PhMe (5 mL). A white precipitate formed, the reaction mixture was stirred for 20 min and filtered. The filtrate was partitioned between EtOAc and saturated aqueous NaHCO3. The layers were separated and the organic was washed with 1 M HCl, water and brine, dried over Na2SO4, filtered and concentrated. The resulting oil, 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate 23 (4.0 g, 98% yield), was used without further purification. LRMS (M+Na)+ Calcd.: 488. found 488.

Provenance & Evidence