Tetrabutylammonium Fluoride → HCID 57743036、化合物

HRID 1926745ノート

反応式

HRID 1926745 の反応式
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[C:5]([CH3:23])[N:4](S(C2C=CC(C)=CC=2)(=O)=O)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[C:5]([CH3:23])[NH:4][N:3]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 53629161HCID 53629161、化合物

生成物 1

HCID 57743036HCID 57743036、化合物収率 14%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
85 °C

実験手順

In a 100 ml flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, 1-({3,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-4-yl}methyl)-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one x61 (0.83 g, 1.7 mmol) is dissolved in THF (40 ml). A 1 M solution of tetrabutylammonium fluoride in THF (1.7 ml, 1.7 mmol) is added and the mixture is heated at 85° C. for 48 h. The solvent is evaporated and the residue is dissolved in water. The aqueous phase is extracted six times with diethylether and the combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by preparative chromatography on silicagel and recrystallized from AcOEt to give 77 mg of 1-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 167.

後処理

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionThe aqueous phase is extracted six times with diethylether
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by preparative chromatography on silicagel
  8. customrecrystallized from AcOEt

出典と根拠

ORDレコード
ord-2382608770d6492f93a84bfa71e94fb9
出典データセット
uspto-grants-2012_05
特許番号
US08183241B2

反応ノート

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