Tert-butyl 2-(4-nitro-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate → Tert-butyl 2-(4-amino-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Participants

Reaction Steps

To a solution of the product of step A (43 mg, 0.08 mmol) in ethanol (5 mL) was added 5% palladium on carbon (60 mg). The reaction flask was purged with hydrogen and the reaction mixture was stirred at ambient temperature for 4 h before it was filtered through a celite bed. The filtrate was concentrated in vacuo to give tert-butyl 2-(4-amino-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (29 mg, 72%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.00 (s, 1H), 7.71 (dd, J=6.9, 1.8 Hz, 2H), 7.29 (s, 1H), 6.62 (dd, J=6.9, 1.8 Hz, 2H), 5.22 (br s, 1H), 4.69 (br s, 1H), 4.04 (s, 2H), 3.82 (s, 3H), 3.34 (br s, 1H), 2.72 (s, 3H), 2.44 (d, J=15.9 Hz, 1H), 2.08-2.37 (m, 2H), 1.86-1.97 (m, 1H), 1.52-1.65 (m, 1H), 1.37 (br s, 9H).

Provenance & Evidence