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

HRID 366539Notes

Reaction equation

HRID 366539 reaction equation
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].Br[CH:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13]>CN(C)C=O.O>[CH3:13][CH:12]([N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79046Sec-octyl bromide, (+-)-HCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 232899883-(2-Octyl)-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-2,4-dione (0.3 g) and 2-bromooctane (0.52 g) in dimethylformamide (5 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 48 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-161626737cb6480f9d6a0773d0159a65
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Reaction notes

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