Potassium Carbonate → 3-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione

Participants

Reaction Steps

To a solution of N-benzylmaleimide (5.0 g, 26.7 mmol) in MeCN (334 ml) was added bromonitromethane (1.87 ml, 26.7 mmol). K2CO3 (3.69 g, 26.7 mmol) was added and the reaction mixture vigorously stirred at r.t. After 4 h an additional portion of bromonitromethane (0.2 ml) was added. Further addition of bromonitromethane (0.2 ml) was added at further 4 h intervals (×4). After 48 h, TLC (50% DCM/heptane) indicated reaction completion. The reaction mixture was evaporated to dryness. The brown residue was purified by column chromatography (100% DCM), giving the title compound as a white solid (3.0 g, 42%). 1H NMR (300 MHz, CDCl3) δ: 3.35 (2H, s), 4.50 (1H, s), 4.55 (2H, s), 7.2-7.4 (5H, m).

Provenance & Evidence