Potassium Carbonate → 3-n-Decyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366531

Reaction equation

HRID 366531 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH:12]12[CH2:17][CH:16]1[C:15](=[O:18])[NH:14][C:13]2=[O:19].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:2]([N:14]1[C:15](=[O:18])[CH:16]2[CH:12]([CH2:17]2)[C:13]1=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 163141-IododecaneHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 232899843-n-Decyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

1-Iododecane (1.21 g) was added to a stirred mixture of 3-azabicyclo[3.1.0]hexane-2,4 dione (0.5 g), potassium carbonate (0.62 g) and tetrabutylammonium bromide (1.45 g) in dichloromethane (50 ml) at room temperature and the resulting mixture was stirred for 24 hours. The mixture was filtered and the filtrate was then washed with water (2×100 ml), dried (MgSO4) and evaporated in vacuo to give a brown oil. The oil was purified by column chromatography on silica gel (100 g) using hexane as eluant. Combination and evaporation of the appropriate fractions gave the title compound as a colourless oil.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was then washed with water (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. customThe oil was purified by column chromatography on silica gel (100 g)
  7. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-b6791d355ab8451faf9e7b93158ea257
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Linked notes

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