Sodium Acetate → (3E)-1-benzyl-3-methoxyimino-5,5-dimethylpyrrolidin-2-one

Participants

Reaction Steps

To a solution of 5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione (3.9036 g, 17.97 mmol) in MeOH (90 mL) was added sodium acetate (1.81 g, 21.54 mmol) and methoxyamine hydrochloride (1.80 g, 21.55 mmol). The solution was stirred overnight and the solvent was then removed in vacuo. The residue was partitioned between DCM (200 mL), sat. aq. NaHCO3, and water. The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to provide crude (3E)-5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione 3-(O-methyloxime) (4.5282 g, >100% crude yield) as a yellow/orange oil. LCMS: (M+H)+: 247.1.

Provenance & Evidence