Iodoethane → 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-[1-(5-{[(2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-5,6,7,8-tetrahydroquinolin-5-ol

HRID 715875Notes

Reaction equation

HRID 715875 reaction equation
[CH2:1](I)[CH3:2].[F:4][C:5]1([F:49])[CH2:10][CH2:9][CH:8]([C:11]2[C:20]3[CH:19]([OH:21])[CH2:18][C:17]([CH3:23])([CH3:22])[CH2:16][C:15]=3[N:14]=[C:13]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[N:35]=[CH:34][C:33]([OH:36])=[CH:32][N:31]=4)[CH2:26][CH2:25]3)[C:12]=2[CH:37]([F:48])[C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)[CH2:7][CH2:6]1>>[F:49][C:5]1([F:4])[CH2:6][CH2:7][CH:8]([C:11]2[C:20]3[CH:19]([OH:21])[CH2:18][C:17]([CH3:22])([CH3:23])[CH2:16][C:15]=3[N:14]=[C:13]([CH:24]3[CH2:25][CH2:26][N:27]([C:30]4[N:35]=[CH:34][C:33]([O:36][CH2:32][C@@H:33]([O:36][CH:2]5[CH2:1][CH2:17][CH2:18][CH2:19][O:21]5)[CH3:34])=[CH:32][N:31]=4)[CH2:28][CH2:29]3)[C:12]=2[CH:37]([F:48])[C:38]2[CH:39]=[CH:40][C:41]([C:44]([F:46])([F:45])[F:47])=[CH:42][CH:43]=2)[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 76372263(-)-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

Product 1

HCID 866824514-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-[1-(5-{[(2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-5,6,7,8-tetrahydroquinolin-5-ol

Procedure

Reactions similar to those of Example 13 were performed except for using (2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methyl benzene sulfonate which was synthesized by the method described in P. Huszthy et al., Journal of Organic Chemistry, 1992, Vol. 57, pp. 5383-5394, instead of ethyl iodide, and from 50 mg (77 μmol) 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 4, 49 mg (62 μmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-[1-(5-{[(2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-5,6,7,8-tetrahydroquinolin-5-ol was obtained.

Workup

  1. customwas synthesized by the method

Sources & evidence

ORD record
ord-03467462c6294fe49fe909fc22e1d169
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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