Triethylamine → 1,1-Dimethylethyl (2S,4R)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylate

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To a solution of (2S,4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (4.72 g, 14.2 mmol) and triethylamine (3.97 mL, 28.5 mmol) in DCM (30 mL) cooled to 0° C. was added methanesulfonyl chloride (1.66 mL, 21.9 mmol). The reaction mixture was stirred overnight while the ice bath was allowed to warm to room temperature. The solvent was removed under reduced pressure and the residue partitioned between EtOAc and water. The organic phase was washed with 1N phosphoric acid (100 mL), water (100 mL), saturated sodium bicarbonate solution (100 mL) and brine (100 mL) and then was dried over magnesium sulfate and concentrated to yield (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate (5.34 g, 13.0 mmol) as a colorless oil. RP-HPLC (Table 1, Method f) Rt 6.25 min; m/z: (M−H)− 468.

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