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

HRID 2363502Notes

Reaction equation

HRID 2363502 reaction equation
[C:1]1([C:7]2([C:12]([OH:14])=O)[CH2:11][CH2:10]CC2)[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)C1C=CC=CC=1>>[CH3:35][CH:11]([CH3:10])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]([NH:29][C@@H:26]1[C@H:24]2[C@H:23]([CH2:22][N:21]([CH2:20][C:19]3[CH:30]=[CH:31][CH:32]=[C:17]([C:16]([F:33])([F:15])[F:34])[CH:18]=3)[CH2:25]2)[CH2:28][CH2:27]1)=[O:14]

Participants

4

Reactant 3

HCID 661671-Phenylcyclopentanecarboxylic acidHCID 66590379(3aS*,4S*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 665909373-methyl-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-methyl-2-phenylbutanoic acid for 1-phenylcyclopentanecarboxylic acid and (3aS*,4S*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine from Step E for (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in Example 1: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.23 (d, J=6.9, 0.5H), 8.13 (d, J=7.1, 0.5H), 7.73 (s, 0.5H), 7.67 (s, 0.5H), 7.63 (dd, J=6.7, 8.0, 2H), 7.56-7.53 (m, 1H), 7.50 (t, J=8.5, 2H), 7.38-7.22 (m, 3H), 4.45-4.38 (m, 0.5H), 4.33-4.26 (m, 0.5H), 3.50 (s, 1H), 3.44 (d, J=13.4, 0.5H), 3.21 (d, J=13.4, 0.5H), 3.17 (d, J=10.5, 0.5H), 3.10 (d, J=10.5, 0.5H), 2.91 (qd, J=3.4, 7.9, 0.5H), 2.79 (dd, J=3.4, 9.5, 0.5H), 2.74-2.56 (m, 1.5H), 2.47-2.31 (m, 2.5H), 2.27 (dd, J=3.1, 8.9, 0.5H), 2.21 (d, J=2.7, 0.5H), 1.98-1.93 (m, 0.5H), 1.89-1.79 (m, 0.5H), 1.74-1.56 (m, 1.5H), 1.53-1.46 (m, 0.5H), 1.46-1.39 (m, 0.5H), 1.30-1.23 (m, 1H), 1.19 (d, J=6.5, 1.5H), 1.17-1.11 (m, 0.5H), 1.08 (d, J=6.5, 1.5H), 0.72 (dd, J=6.7, 9.6, 3H); MS (ESI+) m/z 445 (M+H)+.

Sources & evidence

ORD record
ord-9ad38626b0c340b0aaeaf6f45018290c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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