trans-2-Methyl-8-styryl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bh)-one → trans-2-Methyl-8-phenethyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bh)-one
Reaction equation
[CH3:1][N:2]1[CH2:11][C@@H:10]2[C@H:4]([CH2:5][NH:6][C:7](=[O:24])[C:8]3[CH:15]=[C:14]([CH:16]=[CH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:13]=[CH:12][C:9]=32)[CH2:3]1>[Pd].CO>[CH3:1][N:2]1[CH2:11][C@@H:10]2[C@H:4]([CH2:5][NH:6][C:7](=[O:24])[C:8]3[CH:15]=[C:14]([CH2:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:13]=[CH:12][C:9]=32)[CH2:3]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 50 mL pressure bottle was added a mixture of Example 85 (31.8 mg, 0.100 mmol), 5% palladium on carbon, wet (7.95 mg, 0.075 mmol) and methanol (10 mL). This was stirred for 5 hours under an atmosphere of hydrogen (30 psi) at room temperature. The reaction was complete as indicated by LC/MS. The mixture was filtered through a nylon membrane, concentrated, and purified by silica gel chromatography eluting with a gradient of methanol in dichloromethane (0-20%) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.90 (t, J=3.6, 1H), 7.71 (d, J=1.9, 1H), 7.32-7.12 (m, 6H), 7.06 (d, J=7.8, 1H), 3.27-3.13 (m, 2H), 3.07 (dt, J=9.2, 18.4, 2H), 2.92-2.82 (m, 5H), 2.65-2.56 (m, 2H), 2.35 (d, J=3.9, 3H), 2.20-2.06 (m, 1H); MS (ESI+) m/z 321.0 [M+H]+.
Workup
- filtrationThe mixture was filtered through a nylon membrane
- concentrationconcentrated
- custompurified by silica gel chromatography
- washeluting with a gradient of methanol in dichloromethane (0-20%)
Sources & evidence
- ORD record
- ord-93724194f4db4e21a8ac3e5874882155
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846951B2
Reaction notes
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