O-methylhydroxylammonium chloride → benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate (2.91 g, 11.8 mmol) in MeOH (10 mL) was added sodium acetate (1.93 g, 23.5 mmol) and o-methylhydroxylamine hydrochloride (1.97 g, 23.5 mmol). The mixture was stirred at rt for 18 h. The reaction was concentrated and then diluted with dichloromethane (200 mL). The organic layer was washed with water (20 mL) and aq. sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. (Z)-benzyl 4-(methoxyimino)-3,3-dimethylpyrrolidine-1-carboxylate (3.17 g, 97% yield) was obtained as a colorless oil. m/z: 277.17 (M+H); LC retention time: 2.83 min (analytical HPLC Method I).

Provenance & Evidence