1-Phenylcyclopentanecarboxylic acid → 3,3-dimethyl-2-phenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamide

HRID 1092524Notes

Reaction equation

HRID 1092524 reaction equation
[C:1]1(C2(C(O)=O)CCCC2)C=CC=CC=1.[CH3:15][CH:16]([CH3:46])[CH:17]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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].C(N1C[C@H]2C(N)CC[C@H]2C1)C1C=CC=CC=1>>[CH3:15][C:16]([CH3:1])([CH3:46])[CH:17]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:37])([F:38])[F:39])[CH:31]=3)[CH2:27]2)[CH2:23][CH2:22]1)=[O:19]

Participants

4

Reactant 3

HCID 661671-Phenylcyclopentanecarboxylic acidHCID 665909373-methyl-2-phenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamideHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 546741683,3-dimethyl-2-phenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamide

Procedure

The title compound was prepared by substituting 3,3-dimethyl-2-phenylbutanoic 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 8.32 (d, J=6.7, 0.5H), 8.13 (d, J=7.1, 0.5H), 7.74-7.70 (m, 1H), 7.69-7.66 (m, 1H), 7.61 (t, J=8.6, 3H), 7.48-7.43 (m, 1H), 7.37-7.24 (m, 3H), 4.48-4.39 (m, 0.5H), 4.36-4.28 (m, 0.5H), 3.51 (q, J=13.1, 0.5H), 3.41 (d, J=17.1, 1H), 3.35 (d, J=13.3, 0.5H), 3.13 (d, J=13.4, 0.5H), 2.98 (qd, J=4.0, 8.2, 0.5H), 2.81 (dd, J=3.9, 9.5, 0.5H), 2.74 (ddd, J=3.4, 7.8, 16.6, 0.5H), 2.49-2.37 (m, 2H), 2.31 (dd, J=3.4, 9.6, 0.5H), 2.24-2.15 (m, 2H), 2.01-1.94 (m, 0.5H), 1.84 (ddd, J=8.1, 11.7, 14.5, 0.5H), 1.73-1.65 (m, 1H), 1.64-1.56 (m, 0.5H), 1.52-1.38 (m, 1H), 1.27 (dt, J=5.6, 12.2, 1H), 1.16 (s, 4.5H), 1.11 (s, 4.5H); MS (ESI+) m/z 459 (M+H)+.

Sources & evidence

ORD record
ord-cb037476580641868fc49851977e651b
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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