Ethyl Acetate → N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane

Participants

Reaction Conditions

Reaction Steps

Nitrosonium tetrafluoroborate (2.415 g, 20.67 mmol) was added in several portions to a cooled (−30° C.) solution of 1,1-dimethylethyl cyclopropylcarbamate (2.5 g, 15.90 mmol) in anhydrous Pyridine (4 mL) and Acetonitrile (40 mL). The solution was stirred at −30° C. for 30 minutes then at 0° C. for 2 hours. Ice water and EtOAc were added. The organic phase was separated and washed with 1N HCl, 1N NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. The product was collected as 2.66 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.37-0.79 (m, 4 H), 1.64 (s, 9 H), 2.18-2.41 (m, 1 H).

Provenance & Evidence