Reaction Steps
A solution of (12b-ethyl-9-(4-fluorophenyl)-1,2,6,7,9,12b-hexahydro-5H-9,10-diaza-benzo[3,4]cyclohepta[1,2-f]inden-3-one (8, R1=4-Fluorophenyl, R2=Ethyl) (3.03 g, 8.09 mmol) in toluene (75 mL) containing 20% Pd(OH)2 on carbon (0.290 g, 0.413 mmol) was evacuated and placed under hydrogen. The reaction was shaken under about 55 psi of hydrogen for about 12 h then at about 55° C. for about 6 h. The catalyst was removed by filtration through Celite® and the filtrate was concentrated under reduced pressure. The residue was treated with EtOAc (20 mL) and the solids which formed upon standing were collected by filtration and washed with EtOAc (3 mL). The filtrate was retained. The solid was recrystallized from EtOAc (25 mL) to yield (4aR,12bR)-12b-ethyl-9-(4-fluorophenyl)-1,2,4a,5,6,7,9,12b-octahydro-4H-9,10-diaza-benzo[3,4]cyclohepta[1,2-f]inden-3-one; compound with (4aS,12bS)-12b-ethyl-9-(4-fluoro-phenyl)-1,2,4a,5,6,7,9,12b-octahydro-4H-9,10-diaza-benzo[3,4]cyclohepta[1,2-f]inden-3-one (10, R1=4-Fluorophenyl, R2=Ethyl) (1.26 g, 41%); LC/MS, method 2, Rt=3.05 min, MS m/z 377 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.27 (d, J=0.8 Hz, 1H), 7.86 (s, 1H), 7.83-7.77 (m, 2H), 7.59 (s, 1H), 7.45-7.37 (m, 2H), 3.29-3.24 (m, 1H), 2.99-2.94 (m, 1H), 2.55-2.43 (m, 3H), 2.40-2.11 (m, 3H), 2.09-1.85 (m, 5H), 1.64-1.57 (m, 1H), 1.37-1.28 (m, 1H), 0.49 (t, J=7.3 Hz, 3H).
