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

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Reaction Steps

To a mixture of N-benzylmaleimide (7.40 g) and K2CO3 (5.50 g) in 500 mL of CH3CN was added bromonitromethane (5.60 g) dropwise. The reaction mixture was stirred for 24 h at room temperature and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 4:1 (v/v) PE/EA) to give the title compound as a pale yellow solid (3.90 g, 40.00%), HPLC: 93.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 247.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 3.34 (d, J=1.8 Hz, 2H), 4.51 (t, J=1.6 Hz, 1H), 4.53 (s, 2H), 7.22-7.42 (m, 5H) ppm.

Provenance & Evidence