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Trifluoroacetic acid → Ethyl 2-{8-azabicyclo[3.2.1]octan-3-ylidene}acetate

HRID 1986831
ノート
印刷プレビュー

反応式

HRID 1986831 の反応式
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[CH:16]=[C:11]1[CH2:10][CH:9]2[NH:8][CH:13]([CH2:14][CH2:15]2)[CH2:12]1)[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58968477Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

生成物 1

HCID 58968325Ethyl 2-{8-azabicyclo[3.2.1]octan-3-ylidene}acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (12.3 g, 41.8 mmol) in CH2Cl2 was added TFA (10 ml) and the reaction was stirred for 8 h. The solution was concentrated under reduced pressure, diluted with CH2Cl2, and washed first with 2 M NaOH and followed by brine. The water phases were thereafter back-extracted with EtOAc and the combined organic phase was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude title product was used without further purification (7.04 g, 37.9 mmol, 91%).

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with CH2Cl2
  3. washwashed first with 2 M NaOH
  4. extractionThe water phases were thereafter back-extracted with EtOAc
  5. dry with materialthe combined organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude title product was used without further purification (7.04 g, 37.9 mmol, 91%)

出典と根拠

ORDレコード
ord-d473fa7062834f9086eff94d7c75934e
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07550459B2

反応ノート

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