Sodium Chloride → Ethyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

HRID 2400056Notes

Reaction equation

HRID 2400056 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11]1.[Cl-].[Na+]>CS(C)=O>[O:9]1[C:10]2([CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11]2)[CH2:2]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 277754Ethyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 14578448Ethyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

23.5 g (107 mmol) of trimethylsulphoxonium iodide and 3.3 g of sodium hydride (80% strength in paraffin oil) are initially introduced and 80 ml of absolute dimethyl sulphoxide are added dropwise at 10° C. The mixture is stirred for an hour at room temperature and 15.7 g (100 mmol) of ethyl 3-oxopyrrolidine-1-carboxylate [J. Med. Pharm. Chem. 5, 752 (1962)] in 20 ml of absolute dimethyl sulphoxide are then added dropwise in the course of 15 minutes. The mixture is stirred for one hour at room temperature, poured onto a mixture of ice and saturated sodium chloride solution and extracted using diethyl ether. The ether solutions are washed with sodium chloride solution, dried over Na2SO4, concentrated and distilled.

Workup

  1. stirringThe mixture is stirred for one hour at room temperature
  2. extractionextracted
  3. washThe ether solutions are washed with sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-a21d650cc8ef4d3d9e7797fbc1dd5357
Source dataset
uspto-grants-1995_09
Patent number
US05453422

Reaction notes

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