1,2-Dichloroethane → Tert-butyl 3-(methoxy(methyl)carbamoyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Steps

EDC (2.99 g, 15.6 mmol) was added portion wise to a stirred solution of (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid, (2.0 g, 7.8 mmol), DMAP (10 mg), and N,O-dimethylhydroxylamine hydrochloride (1.52 g, 15.6 mmol) in dichloromethane (20 mL). Triethylamine (4.37 mL, 31.33 mmol) was added dropwise, and the reaction mixture was stirred at room temperature overnight. The resulting solution was poured into water, and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give tert-butyl 3-(methoxy(methyl)carbamoyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (1.7 g, 73%) as a colorless oil, which was used without further purification; m/z for C15H26N2O4 expected 298.2. found 321.3 (M+Na)+, 299.3 (M+H)+.

Provenance & Evidence