Trifluoroacetic acid → HCID 58258845, compound

Participants

Reaction Steps

To a solution of the product of step A (110 mg, 0.30 mmol) in dichloromethane at 0° C. was added trifluoroacetic acid (0.57 ml, 7.5 mmol) and the reaction was stirred overnight. The reaction mixture was made basic with saturated sodium bicarbonate solution and extracted with dichloromethane. The dichloromethane layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was crystallized from dichloromethane to give 2-phenylsulfonyl-5-(2-hydroxy)ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (100 mg, 87%) as a white crystalline solid: 1H NMR (CDCl3, 300 MHz), δ 8.27 (s, 1H), 7.93-7.96 (m, 2H), 7.71 (dd, J=9.0, 1.2 Hz, 1H), 7.52-7.62 (m, 4H), 5.29-5.31 (m, 1H), 4.53 (br s, 1H), 4.24 (t, J=5.1 Hz, 2H), 3.81 (t, J=5.1 Hz, 2H), 3.54 (dd, J=17.4, 4.5 Hz, 1H), 3.12 (d, J=20.7 Hz, 1H), 2.23-2.46 (m, 3H), 1.93-1.97 (m, 1H).

Provenance & Evidence