3-(Trifluoromethyl)benzaldehyde → HCID 46213559, compound
Reaction equation
FC(F)(F)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][NH:24][CH2:25]2)[CH2:21][CH2:20]1)=[O:17].[CH:34]1(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)[CH2:39]CCC[CH2:35]1>>[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][N:24]([CH2:35][CH2:34][CH2:39][C:4]3[CH:3]=[CH:10][CH:9]=[CH:8][C:5]=3[CH3:6])[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Procedure
The title compound was prepared by substituting 3-o-tolylpropanol for 3-(trifluoromethyl)benzaldehyde and 3-methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide from Example 83 Step A for 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide in the procedure described for Example 54: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.57 (dd, J=7.2, 14.2, 1H), 7.68-7.62 (m, 2H), 7.34 (t, J=7.5, 2H), 7.29-7.23 (m, 2H), 7.23-7.22 (m, 1H), 7.17 (dd, J=2.6, 3.9, 2H), 4.42-4.31 (m, 1H), 3.23 (d, J=10.4, 1H), 2.98 (dd, J=2.3, 8.8, 0.5H), 2.69-2.64 (m, 2H), 2.64-2.59 (m, 2H), 2.58-2.51 (m, 0.5H), 2.51-2.45 (m, 0.5H), 2.45-2.39 (m, 0.5H), 2.39-2.34 (m, 2H), 2.32 (dd, J=2.7, 8.9, 1H), 2.28 (s, 1.5H), 2.25 (s, 1.5H), 2.19 (d, J=8.1, 0.5H), 2.17-2.11 (m, 1.5H), 1.93-1.85 (m, 1H), 1.84-1.77 (m, 0.5H), 1.73 (dd, J=7.6, 15.1, 1H), 1.66 (dt, J=7.4, 9.4, 1.5H), 1.43 (dt, J=7.5, 13.8, 1H), 1.38-1.30 (m, 1H), 1.23 (dd, J=6.5, 12.1, 3H), 0.71 (dd, J=2.8, 6.7, 3H); MS (ESI+) m/z 419 (M+H)+.
Sources & evidence
- ORD record
- ord-a7e12e5b73de4cca936e91a44c96f401
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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