Sodium Acetate → benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylate

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Reaction Steps

To a solution of phenylmethyl 3,3-dimethyl-4-oxo-1-pyrrolidinecarboxylate (0.9135 g, 3.694 mmol) in MeOH (37 mL) was added sodium acetate (0.606 g, 7.387 mmol) and O-methylhydroxylamine hydrochloride (0.620 g, 7.397 mmol). The solution was stirred for 3 h, and then concentrated in vacuo. The residue was partitioned between DCM (100 mL), water (5 mL), and sat. aq. NaHCO3 (30 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide phenylmethyl (4Z)-3,3-dimethyl-4-[(methyloxy)imino]-1-pyrrolidinecarboxylate (0.9124 g, 89% yield) as a pale yellow oil. LCMS: (M+H)+: 277.0.

Provenance & Evidence