Trifluoroacetic acid → HCID 67085602, compound

Participants

Reaction Steps

The product of step A was Boc-deprotected with TFA following the procedure of Example 28, Step B. The crude material was purified by flash column chromatography (SiO2, 90:9:1 dichloromethane/methanol/ammonium hydroxide) followed by semi-preparative HPLC. The free base was treated directly with 1.25 M HCl in methanol (2 mL) and the solution concentrated in vacuo to give 2-(3,5-dichlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (15 mg, 31%, AUC HPLC 98.9%) as an off-white solid: mp 190-195° C.; 1H NMR (CD3OD, 300 MHz) δ 8.32 (s, 1H), 7.88 (d, J=1.8 Hz, 2H), 7.58-7.78 (m, 3H), 5.28-5.38 (m, 1H), 4.55 (br s, 1H), 3.72 (s, 3H), 3.40-3.60 (m, 1H), 3.02-3.17 (m, 1H), 2.22-2.55 (m, 3H), 1.92-2.07 (m, 1H); ESI MS m/z 421 [M+H]+.

Provenance & Evidence