3-(Trifluoromethyl)benzaldehyde → 3-methyl-N-[(3aR,4S,6aS)-2-(2-methylbenzyl)octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide
Reaction equation
FC(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].[CH:34]1(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]([CH2:34][C:4]3[CH:3]=[CH:10][CH:9]=[CH:8][C:5]=3[CH3:6])[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 2-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 8.57-8.51 (m, 1H), 7.63 (dd, J=3.5, 7.1, 2H), 7.43-7.36 (m, 1H), 7.36-7.30 (m, 3H), 7.25 (dd, J=6.9, 9.6, 2H), 7.20-7.13 (m, J=10.0, 2H), 4.31 (dd, J=5.5, 11.3, 1H), 3.57 (d, J=13.1, 0.5H), 3.48 (d, J=13.0, 0.5H), 3.39 (d, J=13.0, 0.5H), 3.29 (d, J=13.0, 0.5H), 3.21 (d, J=10.3, 1H), 2.92 (dd, J=2.8, 9.0, 0.5H), 2.68-2.60 (m, 1H), 2.60-2.53 (m, 1H), 2.51-2.45 (m, 1H), 2.35 (s, 1.5H), 2.30 (s, 1.5H), 2.28-2.17 (m, 2H), 2.15-2.06 (m, 1H), 1.84 (ddd, J=6.8, 12.4, 20.0, 1H), 1.76-1.62 (m, 1H), 1.42 (dt, J=7.2, 19.2, 0.5H), 1.33 (dt, J=7.0, 12.5, 0.5H), 1.29-1.22 (m, 0.5H), 1.20 (d, J=6.5, 3H), 0.70 (d, J=6.7, 3H); MS (ESI+) m/z 391 (M+H)+.
Sources & evidence
- ORD record
- ord-f58620cac43a47d6bd23a7d8e967087b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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