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 629367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629367
[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]

Komponenten

8

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 53393272Potassium osmate(VI) dihydrateKatalysatorHCID 962WaterLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-abb84864d3c848f7aa4182f74270c5aa
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315458B2

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