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Nitromethane → Tert-butyl(+/-)-[(1S,5R,6R)-3-propyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

HRID 551628
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HRID 551628 반응식
[CH2:1]([C:4]1[CH2:5][C@@H:6]2[C@H:9]([CH:10]=1)[C:8](=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH2:2][CH3:3].N12CCCN=C1CCCCC2.P([O-])(O)(O)=O.[K+].[N+:36]([CH3:39])([O-:38])=[O:37]>>[CH2:1]([C:4]1[CH2:5][C@@H:6]2[C@H:9]([CH:10]=1)[C@@:8]([CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])([CH2:39][N+:36]([O-:38])=[O:37])[CH2:7]2)[CH2:2][CH3:3]
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참가 물질

5

반응물 4

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516951Monobasic potassium phosphateHCID 86646125Tert-butyl(+/-)-(1S,5R)-3-propyl-bicyclo[3.2.0]hept-3-en-6-ylideneacetate

생성물 1

HCID 131728896Tert-butyl(+/-)-[(1S,5R,6R)-3-propyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

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온도
55 °C

실험 절차

Tert-butyl(±)-(1S,5R)-3-propyl-bicyclo[3.2.0]hept-3-en-6-ylideneacetate (1.81 g, 7.29 mmol) was dissolved in nitromethane (7 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (1.5 mL, 10.2 mmol) was added, and the mixture was heated with stirring at 50 to 60° C. for 8 hours. The mixture was allowed to cool, and a saturated aqueous solution of potassium dihydrogen phosphate was then added thereto, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil substance (2.22 g, 95%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain the compound of interest as a colorless oil substance (2.22 g, 95%)

출처 및 근거

ORD 기록
ord-479156d1aa994a6888e54a94fc48f341
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947738B2

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