HCID 11750111, compound → HCID 25121182, compound

Participants

Reaction Steps

A solution of 3-(4-fluoro-benzoyl)-1,1-dimethyl-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester (1.03 g) in 40 mL of glacial acetic acid containing 370 mg of Adams catalyst was subjected to hydrogenation under atmospheric pressure of hydrogen for 20 hours at room temperature. (Boekelheide, V. and Liu, C-T, J. Am. Chem. Soc. 1952, 74, 4920-4922). The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified first by column chromatography on silica gel eluting with hexane/DCM and then by preparative normal phase HPLC eluting with hexane/DCM. The title compound was obtained as yellow solid (64 mg). 1H-NMR(CDCl3):δ 10.18 (1H, s), 7.64-7.59 (2H, m), 7.41 (1H, s), 7.13-7.07 (2H, m), 4.18 (2H, q), 3.95 (2H, brs), 2.68-2.61 (4H, m), 1.78 (4H, m), 1.39 (6H, s), 1.18 (3H, t); MS (ES): 411 (MH+).

Provenance & Evidence