1-Phenylcyclopentanecarboxylic acid → HCID 46213175, compound

HRID 1092533Notes

Reaction equation

HRID 1092533 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]=1

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 46213175HCID 46213175, compound

Procedure

The title compound was prepared by substituting 3,3-diphenylpropanoic 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 8.28 (d, J=7.4, 1H), 7.74 (s, 1H), 7.45 (t, J=7.7, 1H), 7.38 (dd, J=1.8, 7.4, 4H), 7.28 (dt, J=7.6, 9.4, 4H), 7.20-7.17 (m, 4H), 5.00 (t, J=7.8, 1H), 4.34-4.26 (m, 1H), 3.56 (d, J=13.5, 1H), 3.43 (d, J=13.5, 1H), 3.14 (d, J=7.9, 2H), 2.65 (dd, J=2.1, 8.3, 1H), 2.45-2.36 (m, 1H), 2.36-2.28 (m, 2H), 2.26-2.19 (m, 2H), 1.98-1.89 (m, 1H), 1.72 (ddd, J=6.3, 12.5, 14.5, 1H), 1.43 (dt, J=7.4, 14.1, 1H), 1.34-1.25 (m, 1H); MS (ESI+) m/z 493 (M+H)+.

Sources & evidence

ORD record
ord-892f0a39bb494048803e0942ab9c1afa
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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