(1S*,2R*)-5,5-Difluoro-2-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]cyclohexanol → (1R,2S)-5,5-Difluoro-2-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]cyclohexanol

HRID 337964Notes

Reaction equation

HRID 337964 reaction equation
[F:1][C:2]1([F:23])[CH2:7][C@H:6]([OH:8])[C@@H:5]([C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=2)[CH2:4][CH2:3]1>CCCCCC.C(O)(C)C>[F:23][C:2]1([F:1])[CH2:7][C@@H:6]([OH:8])[C@H:5]([C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 89963182(1S*,2R*)-5,5-Difluoro-2-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]cyclohexanol

Product 1

HCID 89963210(1R,2S)-5,5-Difluoro-2-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

The (1S*,2R*)-5,5-difluoro-2-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]cyclohexanol prepared in Example 143d was optically resolved with CHIRALPAK IA (Daicel Corp.; hexane/isopropanol=8:2) to yield the title compound as a colorless solid.

Sources & evidence

ORD record
ord-716d529bdb674f2aa8db09c7254a377e
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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