Hydrochloric Acid → 2-(2-Methylphenyl)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) followed by semi-preparative HPLC. The free base was treated with 1.25 M HCl in methanol (0.5 mL) and lyophilized to give 2-(2-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (6 mg, 17%, AUC HPLC 96.3%) as a white solid: mp 186-188° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.18 (br s, 2H), 8.30 (d, J=1.5 Hz, 1H), 8.06 (dd, J=7.8, 1.5 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H), 7.45-7.60 (m, 3H), 7.33 (d, J=7.2 Hz, 1H), 5.36 (d, J=3.9 Hz, 1H), 4.47 (br s, 1H), 3.69 (s, 3H), 3.01 (d, J=17.1 Hz, 1H), 2.39 (s, 3H), 2.20-2.33 (m, 2H), 2.07-2.14 (m, 2H), 1.73-1.90 (m, 1H); ESI MS m/z 367 [M+H]+.

Provenance & Evidence