3-(Trifluoromethyl)benzaldehyde → 3-methyl-N-[(3aR,4S,6aS)-2-(3-methylbenzyl)octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide
Reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][NH:24][CH2:25]2)[CH2:21][CH2:20]1)=[O:17].C1(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)CCCCC1>>[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][N:24]([CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([CH3:2])[CH:4]=3)[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 3-methylbenzaldehyde for 3-(trifluoromethyl)benzaldehyde and 3-methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide from Example 83 Step A for 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide in the procedure described for Example 54: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.62-8.50 (m, 1H), 7.64 (d, J=7.5, 2H), 7.33 (td, J=3.7, 7.5, 2H), 7.29-7.23 (m, J=5.5, 11.0, 3H), 7.18 (s, 1H), 7.07 (d, J=7.0, 1H), 4.42-4.29 (m, 1H), 3.60 (d, J=13.1, 0.5H), 3.51 (d, J=13.0, 0.5H), 3.45 (d, J=13.1, 0.5H), 3.33 (d, J=13.0, 0.5H), 3.22 (d, J=10.4, 1H), 2.90 (dd, J=2.9, 8.9, 0.5H), 2.64 (tt, J=6.8, 13.6, 1H), 2.59-2.46 (m, J=5.3, 12.0, 23.8, 2H), 2.44-2.34 (m, 1H), 2.30 (d, J=5.3, 1H), 2.28-2.23 (m, J=8.0, 4H), 2.13 (dt, J=6.3, 12.4, 1H), 1.94-1.78 (m, 1H), 1.78-1.64 (m, 1H), 1.48-1.25 (m, 1.5H), 1.20 (t, J=6.1, 3H), 0.70 (dd, J=1.9, 6.7, 3H); MS (ESI+) m/z 391 (M+H)+.
Sources & evidence
- ORD record
- ord-ea78422035ad4b11a6713fda6ef276a6
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129417B2
Reaction notes
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