Sodium hydride → 3-(7-Octenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366537

Reaction equation

HRID 366537 reaction equation
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18]>CN(C)C=O.O>[CH2:18]([N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 759078-Bromooct-1-eneHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 232899923-(7-Octenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.11 g) was added to a solution of 3-azabicyclo[3.1.0]hexane-2,4dione (0.3 g) and 7-octenyl bromide (0.52 g) in dimethylformamide (5 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 16 hours. The mixture was diluted with water (15 ml) and then extracted with toluene (20 ml). The organic extract was washed with water (15 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by Kugelrohr distillation (boiling point 130-140° C. @ 0.1 mmHg) to give the title compound as a colourless oil.

Workup

  1. extractionextracted with toluene (20 ml)
  2. extractionThe organic extract
  3. washwas washed with water (15 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. distillationThe residue was purified by Kugelrohr distillation (boiling point 130-140° C. @ 0.1 mmHg)

Sources & evidence

ORD record
ord-7d727b454f524e9f834561970a569f2d
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Linked notes

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