Ethyl 5-bromovalerate → 2-{1-[5-(4-Ethoxycarbonylbutoxy)pyrimidin-2-yl]piperidin-4-yl}-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[F:11][C:12]1([F:56])[CH2:17][CH2:16][CH:15]([C:18]2[C:27]3[CH:26]([OH:28])[CH2:25][C:24]([CH3:30])([CH3:29])[CH2:23][C:22]=3[N:21]=[C:20]([CH:31]3[CH2:36][CH2:35][N:34]([C:37]4[N:42]=[CH:41][C:40]([OH:43])=[CH:39][N:38]=4)[CH2:33][CH2:32]3)[C:19]=2[CH:44]([F:55])[C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)[CH2:14][CH2:13]1>>[CH2:9]([O:8][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][O:43][C:40]1[CH:39]=[N:38][C:37]([N:34]2[CH2:33][CH2:32][CH:31]([C:20]3[C:19]([CH:44]([F:55])[C:45]4[CH:50]=[CH:49][C:48]([C:51]([F:52])([F:53])[F:54])=[CH:47][CH:46]=4)=[C:18]([CH:15]4[CH2:16][CH2:17][C:12]([F:11])([F:56])[CH2:13][CH2:14]4)[C:27]4[CH:26]([OH:28])[CH2:25][C:24]([CH3:30])([CH3:29])[CH2:23][C:22]=4[N:21]=3)[CH2:36][CH2:35]2)=[N:42][CH:41]=1)=[O:7])[CH3:10]Participants
3
Reactant 2
Product 1
Procedure
Reactions similar to those of Example 13 were performed except for using ethyl 5-bromovalerate instead of ethyl iodide, and from 85 mg (0.13 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example 10, the crude title compound was obtained. The total amount of the obtained compound was used in Example (23-2).
Sources & evidence
- ORD record
- ord-f5d56e82cbf241779d5faa2172051c51
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187450B2
Reaction notes
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