Hydrochloric Acid → 2-(4-Cyanophenyl)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-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (38 mg, 49%, AUC HPLC >99%) as a white solid: mp 216-218° C.; 1H NMR (D2O, 300 MHz) δ 8.23 (d, J=1.5 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.78 (dd, J=8.4, 1.8 Hz, 2H), 7.62 (dd, J=8.7 Hz, 1.5 Hz, 1H), 7.49 (d, J=8.7 Hz, 1H), 5.23 (d, J=4.8 Hz, 1H), 4.52-4.57 (m, 1H), 3.51 (s, 3H), 3.46 (dd, J=17.7, 4.5 Hz, 1H), 3.01 (d, J=17.4 Hz, 1H), 2.20-2.48 (m, 3H), 1.78-1.94 (m, 1H); APCI MS m/z 378 [M+H]+.

Provenance & Evidence