Hydrochloric Acid → 2-(1-Napthyl)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 C. 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-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (5 mg, 12%, AUC HPLC 97.9%) as a white solid: mp 229-231° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.38 (br s, 1H), 9.02 (br s, 1H), 8.63 (d, J=8.7 Hz, 1H), 8.48 (s, 1H), 8.43 (dd, J=7.2, 1.2 Hz, 1H), 8.28 (d, J=8.1 Hz, 1H), 8.03-8.09 (m, 1H), 8.76 (t, J=7.8 Hz, 1H), 7.57-7.65 (m, 4H), 5.38 (d, J=3.9 Hz, 1H), 4.47 (br s, 1H), 3.64 (s, 3H), 3.34-3.40 (m, 1H), 2.49 (d, J=17.4 Hz, 1H), 2.18-2.33 (m, 2H), 2.03-2.12 (m, 1H), 1.71-1.89 (m, 1H); ESI MS m/z 403 [M+H]+.

Provenance & Evidence