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 1516710ノート

反応式

HRID 1516710 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8903ec2f7e7a47dbb366a0fc4c331d4c
出典データセット
uspto-grants-2012_07
特許番号
US08227511B2

反応ノート

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