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

HRID 715879Notes

Reaction equation

HRID 715879 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([O:15]C2CCCCO2)[CH3:14])(=O)=O)=CC=1.CC1C=CC(S(OC[C@@H](OC2CCCCO2)C)(=O)=O)=CC=1.[F:43][C:44]1([F:88])[CH2:49][CH2:48][CH:47]([C:50]2[C:59]3[CH:58]([OH:60])[CH2:57][C:56]([CH3:62])([CH3:61])[CH2:55][C:54]=3[N:53]=[C:52]([CH:63]3[CH2:68][CH2:67][N:66]([C:69]4[N:74]=[CH:73][C:72]([OH:75])=[CH:71][N:70]=4)[CH2:65][CH2:64]3)[C:51]=2[CH:76]([F:87])[C:77]2[CH:82]=[CH:81][C:80]([C:83]([F:86])([F:85])[F:84])=[CH:79][CH:78]=2)[CH2:46][CH2:45]1>>[F:88][C:44]1([F:43])[CH2:45][CH2:46][CH:47]([C:50]2[C:59]3[CH:58]([OH:60])[CH2:57][C:56]([CH3:61])([CH3:62])[CH2:55][C:54]=3[N:53]=[C:52]([CH:63]3[CH2:64][CH2:65][N:66]([C:69]4[N:74]=[CH:73][C:72]([O:75][CH2:12][C@H:13]([OH:15])[CH3:14])=[CH:71][N:70]=4)[CH2:67][CH2:68]3)[C:51]=2[CH:76]([F:87])[C:77]2[CH:78]=[CH:79][C:80]([C:83]([F:85])([F:84])[F:86])=[CH:81][CH:82]=2)[CH2:48][CH2:49]1

Participants

4

Reactant 3

HCID 11723166(2S)-2-((Tetrahydro-2H-pyran-2-yl)oxy)propyl 4-methylbenzenesulfonateHCID 12778177(2R)-2-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonateHCID 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 86682460(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-{[(2R)-2-hydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Procedure

Reactions similar to those of Example 37 were performed except for using (2R)-2-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonate, which was synthesized by the method described in B. A. Jones et al., Journal of Heterocyclic Chemistry, 1982, Vol. 19, pp. 551-556, instead of (2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonate, and from 50 mg (77 μmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxy pyrimidin-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, 39 mg of the title compound was obtained as a white solid (yield: 71%).

Workup

  1. customwas synthesized by the method

Sources & evidence

ORD record
ord-2324d3d5eafc4dfdbb863024230beff6
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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