(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate → HCID 78140568, compound

HRID 715884Notes

Reaction equation

HRID 715884 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH:12]2[CH2:17]OC(C)(C)[O:14][CH2:13]2)(=O)=O)=CC=1.C1(C)C=CC(S(OC[C@@H]2COC(C)(C)O2)(=O)=O)=CC=1.[F:40][C:41]1([F:85])[CH2:46][CH2:45][CH:44]([C:47]2[C:56]3[CH:55]([OH:57])[CH2:54][C:53]([CH3:59])([CH3:58])[CH2:52][C:51]=3[N:50]=[C:49]([CH:60]3[CH2:65][CH2:64][N:63]([C:66]4[N:71]=[CH:70][C:69]([OH:72])=[CH:68][N:67]=4)[CH2:62][CH2:61]3)[C:48]=2[CH:73]([F:84])[C:74]2[CH:79]=[CH:78][C:77]([C:80]([F:83])([F:82])[F:81])=[CH:76][CH:75]=2)[CH2:43][CH2:42]1>>[F:85][C:41]1([F:40])[CH2:42][CH2:43][CH:44]([C:47]2[C:56]3[CH:55]([OH:57])[CH2:54][C:53]([CH3:58])([CH3:59])[CH2:52][C:51]=3[N:50]=[C:49]([CH:60]3[CH2:61][CH2:62][N:63]([C:66]4[N:71]=[CH:70][C:69]([O:72][CH2:17][CH:12]([CH2:13][OH:14])[CH2:11][OH:10])=[CH:68][N:67]=4)[CH2:64][CH2:65]3)[C:48]=2[CH:73]([F:84])[C:74]2[CH:75]=[CH:76][C:77]([C:80]([F:82])([F:81])[F:83])=[CH:78][CH:79]=2)[CH2:45][CH2:46]1

Participants

4

Reactant 3

HCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 14893699(2,2-Dimethyl-1,3-dioxan-5-yl)methyl 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 78140568HCID 78140568, compound

Procedure

Reactions similar to those of Example 39 were performed except for using (2,2-dimethyl-1,3-dioxan-5-yl)methyl p-toluenesulfonate, which was synthesized with the method described in J. Dubois et al., Tetrahedron, 1991, Vol. 47, pp. 1001-1012, instead of (S)-(+)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate, and from 4.04 g (6.23 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 4, 2.73 g of the title compound was obtained as a white solid (yield: 59%).

Workup

  1. customwas synthesized with the method

Sources & evidence

ORD record
ord-54479c18501e46b9b4e74844a67ecce5
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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