3-[Benzyl(methyl)amino]-3-(aminocarbonyl)azetidine-1-carboxylate → Tert-butyl 3-(aminocarbonyl)-3-(methylamino)azetidine-1-carboxylate

Participants

Reaction Steps

10% wt Palladium on charcoal (160 mg) in ethyl acetate (2 ml) was added to a solution of 3-[benzyl(methyl)amino]-3-(aminocarbonyl)azetidine-1-carboxylate (500 mg, 1.57 mmol) in ethanol (45 ml). After addition of a few drops of saturated hydrogen chloride in dichloromethane, the reaction mixture was stirred at room temperature under 2 bars of hydrogen for 3 hours. Filtration of the catalyst and concentration under reduced pressure afforded tert-butyl 3-(aminocarbonyl)-3-(methylamino)azetidine-1-carboxylate (335 mg, 93%) as a white solid; 1H NMR Spectrum: (CDCl3) 1.44 (s, 9H), 2.35 (s, 3H), 3.71 (d, 2H), 4.29 (brd, 2H), 5.51 (brs, 1H), 6.95 (brs, 1H).

Provenance & Evidence