Hydrochloric Acid → 2-(3-Trifluoromethoxyphenyl)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, 90:9.9:0.1 dichloromethane/methanol/ammonium hydroxide). The free base was treated with 1.25 M HCl in methanol (1 mL) and the solution concentrated in vacuo to give 2-(3-trifluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (30 mg, 34%, AUC HPLC >99%) as an off-white solid: mp 193-196° C.; 1H NMR (CD3OD, 300 MHz): δ 8.31 (m, 1H), 7.91-7.99 (m, 1H), 7.79-7.85 (m, 1H), 7.71-7.78 (m, 1H), 7.58-7.70 (m, 2H), 7.48-7.57 (m, 1H), 5.26-5.34 (m, 1H), 4.50-4.60 (m, 1H), 3.72 (s, 3H), 3.49 (dd, J=17.4, J=4.2 Hz, 1H), 3.07 (d, J=17.7 Hz, 1H), 2.20-2.52 (m, 3H), 1.91-2.03 (m, 1H). ESI MS m/z 437 [M+H]+

Provenance & Evidence