Pyridine → tert-butyl N-(1-carbamoylcyclopropyl)carbamate

Participants

Reaction Steps

To a mixture of 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid (2.00 g, 9.94 mmol), Boc anhydride (2.82 g, 12.9 mmol), ammonium bicarbonate (0.982 g, 12.4 mmol) in 30 mL of acetonitrile at room temperature was added pyridine (0.482 mL, 5.96 mmol). The cloudy, colorless reaction mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was partitioned between 100 mL of ethyl acetate and 30 mL of 1 M HCl. The organic phase was washed with 30 mL of saturated. NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 1.80 g (90%) of (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester as a white solid.

Provenance & Evidence