Water → 4-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 1967368ノート

反応式

HRID 1967368 の反応式
[Si]([O:8][C@H:9]1[CH2:13][C:12](=[O:14])[N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[C@H:10]1[CH3:27])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[OH:8][C@H:9]1[CH2:13][C:12](=[O:14])[N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:24])[F:25])[CH:16]=2)[C@H:10]1[CH3:27]

参加物

5

反応物 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 595569734-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 595569424-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile収率 35.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (5.61 g) in THF (50 mL) was added tetrabutylammonium fluoride-THF solution (20.0 mL, 1 mol/L), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3) to give the title compound as a colorless oil (yield: 1.42 g, 35%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3)

出典と根拠

ORDレコード
ord-3e255e41ae774521909a3d8a251dc5bc
出典データセット
uspto-grants-2013_04
特許番号
US08420694B2

反応ノート

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