Hydrochloric Acid → 2-(4-Methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Participants

Reaction Steps

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) and the product treated directly with 1.25 M HCl in methanol (0.5 mL). After concentration in vacuo the residue was lyophilized to give 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (49 mg, 34%, AUC HPLC 98.0%) as a light-yellow solid: mp 210-212° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.34 (br s, 1H), 9.04 (br s, 1H), 8.32 (s, 1H), 7.85 (dd, J=7.2, 2.1 Hz, 2H), 7.63 (s, 2H), 7.09 (dd, J=7.2, 2.1 Hz, 2H), 5.35 (d, J=3.9 Hz, 1H), 4.48 (br s, 1H), 3.80 (s, 3H), 3.67 (s, 3H), 3.35-3.45 (m, 1H), 3.01 (d, J=17.1 Hz, 1H), 2.18-2.33 (m, 2H), 2.04-2.15 (m, 1H), 1.72-1.86 (m, 1H); ESI MS m/z 383 [M+H]+.

Provenance & Evidence