5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene → 5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:26][C:13]3([CH3:27])[CH2:14][N:15]([CH3:25])[CH2:16][C:17]4[C:18]5[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][C:23]=5[N:11]([C:12]=43)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:26][C:13]3([CH3:27])[CH2:14][N:15]([CH3:25])[CH2:16][C:17]4[C:18]5[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][C:23]=5[N:11]([C:12]=43)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1Participants
3
Procedure
5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene (30 mg, 0.083 mmol) was dissolved in MeOH (4 mL) and the solution was purged with nitrogen. Palladium chloride (15 mg) was added and hydrogen gas was bubbled through the reaction mixture for 2 h. The reaction mixture was filtered through Celite bed and the Celite bed was rinsed with MeOH. The filtrate was concentrated under reduced pressure to obtain 5-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene. 1H NMR, (HCl, salt, CD3OD) δ (ppm): 7.30 (m, 3H), 7.18 (m, 1H), 7.05-6.95 (m, 3H), 4.70 (m, 2H), 4.30 (m, 2H), 4.10 (m, 1H), 3.58-3.40 (m, 2H), 3.15 (s, 3H), 2.42 (s, 3H), 2.30 (m, 2H), 1.90-1.80 (m, 2JH), 1.70 (s, 3H).