Hydrochloric Acid → HCID 67085478, compound

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-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (41 mg, 45%, AUC HPLC >99%) as an off-white solid: mp 220-222° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.42 (br s, 1H), 9.16 (br s, 1H), 8.66 (d, J=1.5 Hz, 1H), 8.43 (d, J=1.5 Hz, 1H), 8.19 (dd, J=8.0 Hz, 2.1 Hz, 1H), 8.08 (d, J=8.7 Hz, 1H), 8.01 (dd, J=8.0 Hz, 2.1 Hz, 1H), 7.88 (dd, J=8.7 Hz, 2.1 Hz, 1H), 7.64-7.75 (m, 4H), 5.36 (d, J=3.9 Hz, 1H), 4.47 (br s, 1H), 3.67 (s, 3H), 3.30-3.42 (m, 1H), 3.00 (d, J=17.1 Hz, 1H), 2.18-2.34 (m, 2H), 2.05-2.15 (m, 1H), 1.70-1.87 (m, 1H); ESI MS m/z 403 [M+H]+.

Provenance & Evidence