1-Iodooctane → 3-Octyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366533

Reaction equation

HRID 366533 reaction equation
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].I[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CN(C)C=O.O>[CH2:12]([N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 37963773-Octyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (1.48 g, 60% in oil) was added to a stirred solution of 3-azabicyclo[3.1.0]hexane-2,4-dione (4.0 g) and 1-iodooctane (8.88 g) in dry dimethylformamide (70 ml) under a nitrogen atmosphere at 0° C. The reaction mixture was stirred at 0° C. for a further 30 minutes and then at room temperature for 16 hours. The mixture was diluted with water (100 ml) and then extracted with ether (150 ml). The organic extract was washed with water (2×70 ml), dried (MgSO4) and evaporated in vacuo to leave a brown oil. The oil was purified by distillation in vacuo (boiling point 146-147° C. @ 0.1 mmHg) to give the title compound as a pale yellow oil.

Workup

  1. waitat room temperature for 16 hours
  2. extractionextracted with ether (150 ml)
  3. extractionThe organic extract
  4. washwas washed with water (2×70 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto leave a brown oil
  8. distillationThe oil was purified by distillation in vacuo (boiling point 146-147° C. @ 0.1 mmHg)

Sources & evidence

ORD record
ord-ce604a25f31d4f88833bc26b8a18e597
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Linked notes

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