Sodium hydride → Ethyl 1-(1-benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylate

HRID 1457999Notes

Reaction equation

HRID 1457999 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH2:9]([O:16][C:17]([N:19]1[CH2:22][CH:21]([C:23](=[CH2:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.[Cl-].[Na+].O>[CH2:9]([O:16][C:17]([N:19]1[CH2:20][CH:21]([C:23]2([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:2][CH2:29]2)[CH2:22]1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 54322358Ethyl 2-(1-benzyloxycarbonyl-3-azetidinyl)acrylate

Product 1

HCID 54249419Ethyl 1-(1-benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylateYield 37%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To 1.27 g (5.76 mmol) of trimethylsulfoxonium iodide dissolved in 10 ml of dimethyl sulfoxide was added 192 mg (4.80 mmol) of 60% sodium hydride, followed by 15 minutes of stirring at room temperature. Thereto was then added 1.39 g (4.80 mmol) of ethyl 2-(1-benzyloxycarbonyl-3-azetidinyl)acrylate which has been dissolved in 10 ml of dimethyl sulfoxide. The resulting mixture was stirred at room temperature for 4 hours and then at 100° C. for 1 hour. The reaction solution was mixed with 200 ml of saturated brine and extracted with ethyl acetate (100 ml×3), and the organic layer was washed with saturated brine (100 ml×2) and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (100 ml, ethyl acetate:hexane=1:2) to yield 536 mg (37%) of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 4 hours
  2. waitat 100° C. for 1 hour
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. washthe organic layer was washed with saturated brine (100 ml×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent
  7. customthe resulting residue was purified by a silica gel column chromatography (100 ml, ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-40016acd816b4fcbac8a34a0fe6da6f8
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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