Sodium Iodide → 1-Methyl-1-azaspiro[4.5]decane-2,8-dione

HRID 2380406Notes

Reaction equation

HRID 2380406 reaction equation
C1O[C:4]2([CH:8](OS(C)(=O)=O)[CH2:7][C:6]3([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)[N:5]2[CH3:20])[O:3]C1.[I-].[Na+]>CC(C)=O>[CH3:20][N:5]1[C:6]2([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH2:7][CH2:8][C:4]1=[O:3]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 54503705HCID 54503705, compound

Product 1

HCID 152296851-Methyl-1-azaspiro[4.5]decane-2,8-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-mesyloxy-1-methyl-1-azaspiro[4.5]decane-2,8-dione ethylene ketal (1.28 g), sodium iodide (1.8 g) and acetone (20 mL) was refluxed with stirring for 90 min. The solvent was removed in vacuo and the residue was dissolved in methylene chloride and washed with water. After drying over magnesium sulfate the solvent was removed in vacuo. The residue was dissolved in toluene (20 mL) and treated with tri-n-butyltin hydride (1.75 g) and AIBN (20 mg) and the resulting mixture was heated at 110° C. for 1 h. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate as the eluent. The resulting product was stirred with a mixture of water (5 mL), 3N HCl (1.5 mL) and acetic acid (2 mL) for 16 h. The resulting product was extracted 3 times with methylene chloride, washed with sodium bicarbonate solution, dried over magnesium sulfate and the solvent was removed in vacuo to afford 1 -methyl-1-azaspiro[4.5]decane-2,8-dione as an oil.

Workup

  1. temperaturewas refluxed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialAfter drying over magnesium sulfate the solvent
  6. customwas removed in vacuo
  7. dissolutionThe residue was dissolved in toluene (20 mL)
  8. additiontreated with tri-n-butyltin hydride (1.75 g) and AIBN (20 mg)
  9. customAfter removal of the solvent the residue
  10. customwas chromatographed on silica gel with ethyl acetate as the eluent
  11. stirringThe resulting product was stirred with a mixture of water (5 mL), 3N HCl (1.5 mL) and acetic acid (2 mL) for 16 h
  12. extractionThe resulting product was extracted 3 times with methylene chloride
  13. washwashed with sodium bicarbonate solution
  14. dry with materialdried over magnesium sulfate
  15. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f9a22319b2e340af9ade3e3e577277ee
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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