Acryloyl chloride → 8-Nitro-8-phenyl-hexahydro-indolizin-5-one

HRID 1097625

Reaktionsgleichung

Reaktionsgleichung von HRID 1097625
[N+:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O-:3])=[O:2].[N:11]1[CH2:12][CH2:13][CH2:14][CH:15]=1.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18]>O1CCOCC1>[N+:1]([C:4]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:12]2[N:11]([CH2:15][CH2:14][CH2:13]2)[C:16](=[O:19])[CH2:17][CH2:18]1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 13140Acryloyl chlorideHCID 69321(Nitromethyl)benzeneHCID 798031-Pyrroline

Produkt 1

HCID 585679098-Nitro-8-phenyl-hexahydro-indolizin-5-oneAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a room temperature solution of 280 mg (2.042 mmol) nitromethyl-benzene in 3 ml dioxane was added a solution of 141 mg (2.042 mmol) 3,4-dihydro-2H-pyrrole (CAS: 638-31-3) in 0.5 ml dioxane. The mixture was stirred at room temperature for 10 min then at 60° C. for 2.5 hours then cooled to 5-10° C. and 198.2 ul (2.45 mmol) acryloyl chloride was added dropwise. The mixture was then warm to room temperature and stirred for 1 hour. The reaction mixture was quenched with saturated sodium bicarbonate and ethylacetate. The aqueous phase was extracted two times with ethylacetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 511 mg of light yellow oil. The crude compound was purified with flash column chromatography on silica eluting from n-heptane and ethyl acetate (0 to 40%) to provide 332 mg of an oil that was dissolved in 3 ml dioxane and 816 mg of amberlyst A-21 was added. The reaction mixture was heated to 70° C. overnight cooled to room temperature, amberlyst was filtered and washed with ethylacetate. The filtrate was concentrated in vacuo. The crude compound was purified with flash column chromatography on silica eluting from n-heptane and ethyl acetate (0 to 100%) to provide 329 mg (y: 62%) of title compound as a colorless oil. (M+H+: 261.1)

Aufarbeitung

  1. temperatureat 60° C. for 2.5 hours then cooled to 5-10° C.
  2. temperatureThe mixture was then warm to room temperature
  3. stirringstirred for 1 hour
  4. customThe reaction mixture was quenched with saturated sodium bicarbonate and ethylacetate
  5. extractionThe aqueous phase was extracted two times with ethylacetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7fe32c210217481686f104d122603349
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143273B2

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