Borane → 3-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Participants

Reaction Steps

To a solution of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione (6.00 g) in THF was added a solution of borane in THF (1 M, 100 mL) dropwise. The reaction mixture was refluxed for 1 h, then cooled to rt and quenched with MeOH. The mixture was concentrated in vacuo and the residue was chromatographed by a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to afford the title compound as pale yellow oil (4.30 g, 80.00%), HPLC: 94.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 219.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.51 (m, 2H), 3.14 (d, J=1.8 Hz, 2H), 3.60 (s, 2H), 4.63 (s, 1H), 7.3 (m, 5H) ppm.

Provenance & Evidence