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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551628
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 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

Produkt 1

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

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-479156d1aa994a6888e54a94fc48f341
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947738B2

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