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 629367노트

반응식

HRID 629367 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 53393272Potassium osmate(VI) dihydrate촉매HCID 962Water용매HCID 24477Sodium Thiosulfate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abb84864d3c848f7aa4182f74270c5aa
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315458B2

반응 노트

불러오는 중…