Ammonium Chloride → Tert-butyl 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Participants

Reaction Steps

A mixture of the product of step A (145 mg, 0.29 mmol), iron powder (82 mg, 1.45 mmol) and ammonium chloride (17 mg, 0.32 mmol) was taken up in ethanol (2.3 mL) and water (1.1 mL). The mixture was refluxed for 3 h then diluted with water and extracted with dichloromethane. The organic extract was dried over sodium sulfate and concentrated in vacuo to give tert-butyl 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (130 mg, 96%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.15 (s, 1H), 7.69-7.71 (m, 2H), 7.62 (d, J=9.3 Hz, 1H), 7.27 (d, J=8.7 Hz, 1H), 6.60-6.65 (m, 2H), 5.24 (br s, 1H), 4.69 (br s, 1H), 4.04 (br s, 2H), 3.58 (s, 3H), 3.48 (br s, 1H), 2.48 (d, J=16.5 Hz, 1H), 2.12-2.32 (m, 2H), 1.89-1.97 (m, 1H), 1.52-1.64 (m, 1H), 1.37 (br s, 9H).

Provenance & Evidence