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

HRID 1681586Notes

Reaction equation

HRID 1681586 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-883f579e0d124d9eb384d6793d91e99a
Source dataset
uspto-grants-1992_12
Patent number
US05173484

Reaction notes

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