Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one → 5-Cyclopentyl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516710노트

반응식

HRID 1516710 반응식
[C:1]1([C:6]2[C:15]([CH:16](O)[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([CH:28]([CH3:30])[CH3:29])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:32])([CH3:31])[O:11]3)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:6]2[C:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[C:14]([CH:28]([CH3:29])[CH3:30])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:31])([CH3:32])[O:11]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 1

HCID 58002986Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

생성물 1

HCID 580030055-Cyclopentyl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzyl]-2,3-dihydro-4H-chromen-4-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of 60 mg (130 μmol) of 5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]-methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 36A) and 14 mg of palladium-on-carbon (10%) in 10 ml of ethanol is stirred under a hydrogen atmosphere at atmospheric pressure overnight. The suspension is filtered through Celite, the filter cake is washed with ethanol and the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 40:1).

후처리

  1. filtrationThe suspension is filtered through Celite
  2. washthe filter cake is washed with ethanol
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 40:1)

출처 및 근거

ORD 기록
ord-8903ec2f7e7a47dbb366a0fc4c331d4c
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227511B2

반응 노트

불러오는 중…