Water → 3-(4-Chlorobut-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366532

Reaktionsgleichung

Reaktionsgleichung von HRID 366532
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].[Cl:11][CH2:12][CH2:13][CH2:14][CH:15](I)CCCC.O>CN(C)C=O>[Cl:11][CH2:12][CH2:13][CH2:14][CH2:15][N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dioneHCID 232899781-Chloro-4-iodooctane

Produkt 1

HCID 232899863-(4-Chlorobut-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.11 g, 60% dispersion in oil) was added to a stirred solution of 3-azabicyclo[3.1.0]hexane-2,4-dione (0.5 g) and 1-chloro-4-iodooctane (0.98 g) in dry dimethylformamide (50 ml) under a nitrogen atmosphere at room temperature. The resulting mixture was stirred for 48 hours and water (50 ml) was then added dropwise. The aqueous mixture was extracted with dichloromethane (2×200 ml) and the combined organic extracts were then washed with water (2×400 ml), dried (MgSO4) and evaporated in vacuo to give an oil. The oil was purified by chromatography on silica (80 g) using 1:1 ethyl acetate/hexane as eluant to give the title compound as a colourless oil.

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with dichloromethane (2×200 ml)
  2. washthe combined organic extracts were then washed with water (2×400 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oil
  6. customThe oil was purified by chromatography on silica (80 g)

Quellen und Nachweise

ORD-Eintrag
ord-f61baab36b774972a71ac6203a4fc40d
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130241

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