1,2-Dichloroethane → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a solution containing 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (60.4 g, 0.30 mol), hydroxybenzotriazole (49 g, 0.36 mol), EDC (69.4 g, 0.36 mol), and triethyamine (142 ml) in 620 ml of dichloromethane was added N,O-dimethylhydroxyl-amine hydrochloride (35.4 g, 0.36 mol). The mixture obtained was stirred overnight at room temperature. The solution was partitioned between 500 ml of water and 200 ml of dichloromethane, and the aqueous layer was washed with 200 ml of dichloromethane. The combined organic layers were washed with 250 ml of brine, dried over magnesium sulfate, filtered and concentrated to afford tert-butyl 3-{[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate, which was used without additional purification.

Provenance & Evidence