Ammonium Chloride → HCID 67085964, compound

Participants

Reaction Steps

To a solution of the product of step A (48 mg, 0.09 mmol) in EtOH (2 mL) and water (1 mL) was added iron powder (27 mg, 0.48 mmol) and ammonium chloride (5.7 mg, 0.10 mmol). The mixture was heated at reflux for 3 h, cooled to ambient temperature and filtered through a celite bed. The filtrate was extracted with chloroform and the organic layer dried over sodium sulfate then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate) to give tert-butyl 2-(3-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (28 mg, 62%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (s, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.29 (d, J=8.7 Hz, 2H), 7.17-7.23 (m, 2H), 6.74 (dd, J=7.3, 1.2 Hz, 1H), 5.17-5.36 (m, 1H), 4.57-4.88 (m, 1H), 3.85 (s, 2H), 3.60 (s, 3H), 3.28-3.40 (m, 1H), 2.48 (d, J=16.5 Hz, 1H), 2.17-2.33 (m, 2H), 1.91-1.97 (m, 1H), 1.54-1.65 (m, 1H), 1.37 (br s, 9H).

Provenance & Evidence