1,1'-Carbonyldiimidazole → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

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Reaction Steps

Add in one portion 1,1′-carbonyldiimidazole (8.3 g, 51 mmol) to a solution of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (10.0 g, 46.5 mmol) in dichloromethane (155 mL) at RT. Allow the mixture to stir for 15 min. Add slowly N,O-dimethylhydroxylamine hydrochloride (5.4 g, 55.8 mmol). Stir the reaction mixture at RT overnight. Dilute the mixture with dichloromethane (200 mL), wash with water (2×300 mL), brine (200 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph and elute with 50-100% ethylacetate/hexane to give 10.8 g (90%) of the title compound. LC-MS/ES m/z 203.0 [M-tert-Bu+H]+.

Provenance & Evidence