3-Methyl-2-phenylbutanoic acid → 2,2-dicyclohexyl-N-{(3aR,4R,6aS)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}acetamide
Reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](O)=[O:5].[F:14][C:15]([F:33])([F:32])[C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][N:20]1[CH2:24][C@@H:23]2[C@H:25]([NH2:28])[CH2:26][CH2:27][C@@H:22]2[CH2:21]1.[CH2:34](N1C[C@H]2[C@@H](N)CC[C@H]2C1)[C:35]1C=CC=C[CH:36]=1>>[CH:7]1([CH:3]([CH:2]2[CH2:13][CH2:36][CH2:35][CH2:34][CH2:1]2)[C:4]([NH:28][C@H:25]2[C@@H:23]3[C@@H:22]([CH2:21][N:20]([CH2:19][C:18]4[CH:29]=[CH:30][CH:31]=[C:16]([C:15]([F:32])([F:14])[F:33])[CH:17]=4)[CH2:24]3)[CH2:27][CH2:26]2)=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 2,2-dicyclohexylacetic acid for 3-methyl-2-phenylbutanoic acid in and (3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine from Step A for (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Step D of Example 14: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.73 (s, 1H), 7.66 (d, J=7.7, 1H), 7.55 (d, J=7.3, 2H), 7.50 (t, J=7.7, 1H), 4.50-4.43 (m, 1H), 3.54 (d, J=12.9, 1H), 3.46 (d, J=12.9, 1H), 2.74 (td, J=2.6, 10.5, 2H), 2.51-2.42 (m, 2H), 2.31 (t, J=8.3, 1H), 2.20 (dd, J=7.8, 9.8, 1H), 1.94-1.54 (m, 15H), 1.46 (d, J=13.0, 1H), 1.40 (d, J=14.4, 1H), 1.35-1.07 (m, 9H), 0.98 (qd, J=3.0, 12.3, 1H); MS (ESI+) m/z 491 (M+H)+.
Sources & evidence
- ORD record
- ord-bc14552517b849d2acc0a0ca631e6d93
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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