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

HRID 1191498
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HRID 1191498 반응식
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]
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-d1118f585cf449beb376087e9e2122da
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680115B2

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