Water → HCID 24986663、化合物

HRID 906981ノート

反応式

HRID 906981 の反応式
[CH3:1][C@H:2]1[C@@:6]([CH3:8])([OH:7])[CH2:5][CH2:4][NH:3]1.[F:9][C:10]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C(=O)([O-])[O-].[Li+].[Li+].O>CS(C)=O>[F:9][C:10]1[CH:17]=[C:16]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH3:8])[C@@H:2]2[CH3:1])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

参加物

6

反応物 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 775452,4-DifluorobenzonitrileHCID 59556870(2S,3S)-2,3-dimethylpyrrolidin-3-ol

生成物 1

HCID 24986663HCID 24986663、化合物収率 57%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution (2 mL) of (2S,3S)-2,3-dimethylpyrrolidin-3-ol 0.5 oxalate (228 mg), 2,4-difluorobenzonitrile (292 mg) and lithium carbonate (206 mg) in DMSO was stirred at 80° C. for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) and recrystallized from hexane-isopropyl ether to give the title compound as a colorless solid (yield: 188 mg, yield: 57%).

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 sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)
  6. customrecrystallized from hexane-isopropyl ether

出典と根拠

ORDレコード
ord-3596dd5b86544e2baebcd801e2eccfac
出典データセット
uspto-grants-2011_09
特許番号
US08013008B2

反応ノート

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