1-Phenylcyclopentanecarboxylic acid → 3,3-diphenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}propanamide
Reaction equation
[C:1]1([C:7]2([C:12](O)=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)C(C1C=CC=CC=1)[C:18]([NH:20][C@@H:21]1[C@H:28]2[C@H:24]([CH2:25][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[CH2:27]2)[CH2:23][CH2:22]1)=[O:19].[CH2:47](N1C[C@H]2C(N)CC[C@H]2C1)[C:48]1C=CC=CC=1>>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][C:18]([NH:20][C@@H:21]2[C@H:28]3[C@H:24]([CH2:25][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=4)[CH2:27]3)[CH2:23][CH2:22]2)=[O:19])[CH:10]=[CH:9][CH:8]=[CH:48][CH:47]=1Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 3,3-diphenylpropanoic acid for 1-phenylcyclopentanecarboxylic acid and (3aS*,4S*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 122 Step E for (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described for Example 1: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.10 (d, J=7.0, 1H), 7.72 (s, 1H), 7.62 (d, J=7.8, 1H), 7.48 (t, J=7.7, 1H), 7.39 (dd, J=2.6, 7.5, 5H), 7.26 (dt, J=7.6, 15.1, 5H), 7.17 (dd, J=6.2, 13.5, 2H), 4.38-4.27 (m, 1H), 3.54 (d, J=13.4, 1H), 3.38 (d, J=13.4, 1H), 3.15-3.09 (m, 2H), 2.75 (qd, J=3.6, 7.9, 1H), 2.44-2.35 (m, 2H), 2.32 (t, J=8.3, 1H), 2.20 (dd, J=3.3, 8.9, 1H), 2.08 (dd, J=7.8, 9.5, 1H), 1.70 (t, J=7.9, 1H), 1.58-1.46 (m, 2H), 1.18-1.10 (m, 1H); MS (ESI+) m/z 493 (M+H)+.
Sources & evidence
- ORD record
- ord-6a473a2e70454ca7a8c22045b625b910
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129417B2
Reaction notes
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