Ethyl Acetate → 8-Benzyl-8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]

HRID 40700

Reaktionsgleichung

Reaktionsgleichung von HRID 40700
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH2:9]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][C:19](=[O:24])[CH2:20]2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25](OCC)(=O)C>CS(C)=O>[CH2:9]([N:16]1[CH:17]2[CH2:23][CH2:22][CH:21]1[CH2:20][C:19]1([CH2:18]2)[CH2:25][O:24]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-one

Produkt 1

HCID 866598298-Benzyl-8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Trimethyl sulfoxonium iodide (3.07 g, 13.9 mmol) is placed in 18 ml of DMSO under nitrogen in the presence of sodium hydride dispersed at 60% in oil (0.56 g, 13.9 mmol). After stirring for 30 min at ambient temperature, 8-benzyl-8-aza-bicyclo[3.2.1]octan-3-one (2.0 g, 9.3 mmol) solubilized in 3 ml of DMSO is slowly added. The reaction medium is kept stirring for 4 h and then kept without stirring for 60 h, After hydrolysis, and extraction with ethyl acetate, the organic phase is washed with a saturated aqueous sodium chloride solution and dried over MgSO4. 2.04 g of 8-benzyl-spiro[8-azabicyclo[3.2.1]octane-3,2′-oxirane], subsequently used as it is, are obtained.

Aufarbeitung

  1. additionis slowly added
  2. stirringThe reaction medium is kept stirring for 4 h
  3. stirringwithout stirring for 60 h
  4. washthe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-752f31fa474c4665ac632012bf329c96
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530477B2

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