1,3-Cyclopentanedione → HCID 24993630, compound

HRID 1991369Notes

Reaction equation

HRID 1991369 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:24][CH2:23][C@H:22]3[C@@H:18]([CH2:19][NH:20][CH2:21]3)[C@@H:17]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:34]1(=O)[CH2:38][CH2:37][C:36](=[O:39])[CH2:35]1>>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:24][CH2:23][C@H:22]3[C@@H:18]([CH2:19][N:20]([C:34]4[CH2:38][CH2:37][C:36](=[O:39])[CH:35]=4)[CH2:21]3)[C@@H:17]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:8]=1

Participants

3

Reactant 2

HCID 774661,3-CyclopentanedioneHCID 21099338HCID 21099338, compound

Product 1

HCID 24993630HCID 24993630, compound

Procedure

The title compound was prepared from (3aR,4R,5S,7aS)-5-{(1R)-1-[3,5-bis(tri-fluoromethyl)phenyl]ethoxy}-4-(2-methylphenyl)octahydro-1H-isoindole (step L) and cyclopentane-1,3-dione according to the procedure of Example 7. 1H-NMR (CDCl3): rotamers δ: 7.64 (1H, s), 7.18 (2H, s), 7.04-6.97 (4H, m), 4.74, 4.53 (1H, s), 4.42 (1H, m), 3.68, 3.43 (1H, m), 3.50 (1H, m), 3.06 (1H, m), 2.93 (2H, m), 2.86, 2.76 (1H, m), 2.57 (1H, m), 2.40 (2H, m), 2.28 (3H, s), 2.20 (1H, m), 2.17 (1H, m), 2.10-1.94 (3H, m), 1.58 (1H, m), 1.40 (1H, m), 1.28 (3H, d, J=6.0 Hz). MS: (MH)+552.43

Sources & evidence

ORD record
ord-092093eb7a83435984a601d11f80a4cb
Source dataset
uspto-grants-2010_01
Patent number
US07645790B2

Reaction notes

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