Imidazole → (2R,3S)-3-tert-butyldimethylsilanyloxy-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl Ester

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Reaction Steps

To a solution of compound 3A (0.591 g, 2.27 mmol) in CH2Cl2 (6.5 mL) at rt was added imidazole (0.464 g, 6.81 mmol) followed by tert-butydimethylsilyl chloride (1.71 g, 11.4 mmol). After stirring overnight, the reaction mixture was partitioned between H2O and CH2Cl2. The CH2Cl2 layer was washed with 1 M H3PO4 and water, then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 30% EtOAc/hexane to yield compound 3B (0.519 g). LC/MS m/z 396 [M+Na]+.

Provenance & Evidence