Hydrochloric Acid → HCID 67085230, compound

Participants

Reaction Steps

The product of step B was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 27, step D. The crude material was purified by flash column chromatography (SiO2, 99:0.9:0.1 to 80:18:2 dichloromethane/methanol/ammonium hydroxide) and semi-preparative HPLC. The free base was dissolved in methanol and treated with an excess of HCl in diethyl ether. The solution was concentrated in vacuo and the residue lyophilized from water/acetonitrile to give 2-phenylsulfonyl-5-ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (28 mg, 100%, AUC HPLC >99%) as a white solid: mp 200-204° C. dec; 1H NMR (CD3OD, 300 MHz) δ 8.28 (d, J=1.8 Hz, 1H), 7.91-7.98 (m, 2H), 7.72 (dd, J=8.7; 1.8 Hz, 1H), 7.49-7.63 (m, 4H), 5.25-5.32 (m, 1H), 4.49-4.58 (m, 1H), 4.10-4.28 (m, 2H), 3.42-3.56 (m, 1H), 3.00-3.11 (m, 1H), 2.23-2.52 (m, 3H), 1.88-2.05 (m, 1H), 1.32 (t, J=7.2 Hz, 3H); ESI MS m/z 367 [M+H]+

Provenance & Evidence