3-(Trifluoromethyl)benzaldehyde → N-{(3aS,4R,6aR)-2-[3,5-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-2,2-dicyclohexylacetamide

HRID 2363470Notes

Reaction equation

HRID 2363470 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH:13]1([CH:19]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:20]([NH:22][C@H:23]2[C@H:30]3[C@H:26]([CH2:27][NH:28][CH2:29]3)[CH2:25][CH2:24]2)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)CCCCC1>>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:2]([F:12])([F:11])[F:1])[CH:10]=1)[CH2:6][N:28]1[CH2:29][C@H:30]2[C@H:23]([NH:22][C:20](=[O:21])[CH:19]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:24][CH2:25][C@H:26]2[CH2:27]1

Participants

4

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 462130532,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamideHCID 546741702,2-dicyclohexyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide

Product 1

HCID 86641973N-{(3aS,4R,6aR)-2-[3,5-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-2,2-dicyclohexylacetamide

Procedure

The title compound was prepared by substituting 3,5-bis(trifluoromethyl)benzaldehyde for 3-(trifluoromethyl)benzaldehyde and 2,2-dicyclohexyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide from Example 74 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 8.16 (d, J=7.1, 1H), 7.99 (s, 3H), 4.50-4.42 (m, 1H), 3.69 (d, J=13.9, 1H), 3.54 (d, J=13.9, 1H), 2.92 (dd, J=2.7, 9.0, 1H), 2.65-2.56 (m, J=10.2, 15.6, 2H), 2.55-2.50 (m, 1H), 2.31 (d, J=4.2, 2H), 2.10 (dq, J=5.9, 11.8, 1H), 2.03 (t, J=7.4, 1H), 1.99-1.83 (m, 5H), 1.80 (d, J=12.4, 2H), 1.75-1.64 (m, J=12.4, 18.4, 5H), 1.63-1.56 (m, J=8.7, 2H), 1.44 (td, J=7.6, 21.0, 3H), 1.31-1.16 (m, 4H), 1.16-1.04 (m, 4H); MS (ESI+) m/z 559 (M+H)+.

Sources & evidence

ORD record
ord-db89c1e571fd4687b48a941622602351
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

Loading…