3-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole → HCID 10688060, compound

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Reaction Steps

A solution of 13 (200 mg, 0.55 mmol) in THF (15 mL) was hydrogenated over PtO2 at 55 psi for 1.5 h. The catalyst was removed, the solvent was evaporated, and the resulting solid was triturated with petroleum ether to give 5-amino-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (166 mg, 90%), mp >200° C. 1H NMR [(CD3)2SO] δ 8.01 (d, J=8.4 Hz, 1 H, H-6), 7.64 (d, J=8.3 Hz, 1 H, H-9), 7.45-7.25 (underlying br s, 1 H, H-4), 7.40 (t, J=7.4 Hz, 1 H, H-8), 7.20 (t, J=7.4 Hz, 1 H, H-7), 7.91 (s, 2 H, NH2), 4.11-3.87 (m, 4 H, H-1,2, CHHCl), 3.66 (dd, J=10.5, 8.3 Hz, 1 H, CHHCl), 1.53 (s, 9 H, C(CH3)3).

Provenance & Evidence