2-Chloroethyl chloroformate → 6-Nitro-3-azabicyclo[3.1.0]hexane hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (2.47 g, 11.3 mmol) in 1,2-dichloroethane (5 ml) was added chloroethylchloroformate (1.83 ml, 16.9 mmol) at 0° C. The reaction mixture was heated to 55° C. for 4 h. Further chloroethylchloroformate (0.5 ml) was added and heating continued for 2 h. The reaction mixture was evaporated to dryness. MeOH (15 ml) was added and the reaction mixture was heated at 65° C. for 3 h. Conc. HCl (1 ml) was added and the reaction stirred at r.t. for 2 h. A grey precipitate had formed, this was isolated by filtration and washed with Et2O. The title compound was obtained as a grey powder (464 mg, 25%). 1H NMR (300 MHz, d6-DMSO) δ: 2.90 (2H, s), 3.3-3.6 (4H, m), 4.75 (1H, s), 9.50 (2H, br s).

Provenance & Evidence