Hydrochloric Acid → 2-(3-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). The free base was treated with 1.25 M HCl in methanol (0.5 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(3-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (52 mg, 46%, AUC HPLC >99%) as a white solid: mp 194-196° C.; 1H NMR (D2O, 300 MHz) δ 8.18 (s, 1H), 7.61-7.73 (m, 2H), 7.58 (d, J=9.3 Hz, 1H), 7.30-7.49 (m, 3H), 5.20 (d, J=4.5 Hz, 1H), 4.54 (br s, 1H), 3.55 (s, 3H), 3.42 (dd, J=17.4, 4.2 Hz, 1H), 2.94 (d, J=17.7 Hz, 1H), 2.29-2.45 (m, 2H), 2.24 (s, 3H), 2.05-2.19 (m, 1H), 1.72-1.90 (m, 1H); APCI MS m/z 367 [M+H]+.

Provenance & Evidence