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

HRID 366532

Reaction equation

HRID 366532 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f61baab36b774972a71ac6203a4fc40d
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Linked notes

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