Acetone → rac-4-chloro-3-hydroxy-2-[trans-2-hydroxycyclohexyl]-6-[4-(1H-pyrazol-1-yl)benzyl]-5-(trifluoromethyl)-2,3-dihydro-1H-isoindol-1-one

HRID 629367Notes

Reaction equation

HRID 629367 reaction equation
[Cl:1][C:2]1[C:3]([CH:34]=C)=[C:4]([CH:15]=[C:16]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:25][CH:24]=2)[C:17]=1[C:18]([F:21])([F:20])[F:19])[C:5]([NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])=[O:6].CC(C)=[O:38].C(#N)C.I([O-])(=O)(=O)=O.[Na+]>S([O-])([O-])(=O)=S.[Na+].[Na+].O.O.[O-][Os]([O-])(=O)=O.[K+].[K+].O>[Cl:1][C:2]1[C:17]([C:18]([F:20])([F:21])[F:19])=[C:16]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:27][CH:28]=2)[CH:15]=[C:4]2[C:3]=1[CH:34]([OH:38])[N:7]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])[C:5]2=[O:6]

Participants

8

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 118468373rac-3-chloro-2-ethenyl-N-(trans-2-hydroxycyclohexyl)-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzamide

Product 1

HCID 118468232rac-4-chloro-3-hydroxy-2-[trans-2-hydroxycyclohexyl]-6-[4-(1H-pyrazol-1-yl)benzyl]-5-(trifluoromethyl)-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 3

HCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of rac-3-chloro-2-ethenyl-N-(trans-2-hydroxycyclohexyl)-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzamide (0.07 g) in a mixed solvent of acetone (2.00 mL)-acetonitrile (2.00 mL)-water (2.00 ml) were added potassium osmate(VI) dihydrate (4.00 mg) and sodium periodate (0.08 g), and the mixture was stirred for 16 hr. The reaction mixture was diluted with aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give rac-4-chloro-3-hydroxy-2-[trans-2-hydroxycyclohexyl]-6-[4-(1H-pyrazol-1-yl)benzyl]-5-(trifluoromethyl)-2,3-dihydro-1H-isoindol-1-one (0.05 g) as a crude product. This compound was used in the next step without an additional purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-abb84864d3c848f7aa4182f74270c5aa
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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