1-Phenylcyclopentanecarboxylic acid → 2,2-diphenyl-N-{(3aS*,4R*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}acetamide
Reaction equation
[C:1]1([C:7]2([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:34])([F:33])[C:17]1[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=1)[CH2:20][N:21]1[CH2:25][C@H:24]2[C@H:26]([NH2:29])[CH2:27][CH2:28][C@H:23]2[CH2:22]1.[CH2:35](N1C[C@H]2C(N)CC[C@H]2C1)[C:36]1C=CC=CC=1>>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]([NH:29][C@H:26]2[C@H:24]3[C@H:23]([CH2:22][N:21]([CH2:20][C:19]4[CH:30]=[CH:31][CH:32]=[C:17]([C:16]([F:33])([F:15])[F:34])[CH:18]=4)[CH2:25]3)[CH2:28][CH2:27]2)=[O:14])[CH:10]=[CH:9][CH:8]=[CH:36][CH:35]=1Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 2,2-diphenylacetic acid for 1-phenylcyclopentanecarboxylic acid and (3aS*,4R*,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 2: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.94 (d, J=6.8, 1H), 7.74 (s, 2H), 7.64 (d, J=7.8, 4H), 7.47-7.40 (m, 1H), 7.38-7.29 (m, 5H), 7.28-7.23 (m, 3H), 4.45-4.37 (m, 1H), 3.57 (d, J=13.5, 1H), 3.42 (d, J=13.5, 1H), 2.76 (dd, J=3.0, 9.1, 1H), 2.54-2.47 (m, 1H), 2.47-2.42 (m, 1H), 2.39 (dd, J=7.3, 9.0, 1H), 2.23 (d, J=3.0, 2H), 2.06 (dq, J=6.2, 12.2, 1H), 1.83-1.74 (m, 1H), 1.59 (dt, J=6.9, 14.5, 1H), 1.33 (dt, J=6.3, 19.6, 1H); MS (ESI+) m/z 479 (M+H)+.
Sources & evidence
- ORD record
- ord-e7c734f8c7c949008c4f95e1b1769928
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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