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

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.

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)

ORD-Eintrag

ord-40016acd816b4fcbac8a34a0fe6da6f8

Quelldatensatz

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05849757