Reacción #68978

Ecuación de reacción

Trimethyl sulfoxonium iodide

ethyl acetate

8-benzyl-8-aza-bicyclo[3.2.1]octan-3-one

sodium hydride

→

8-Benzyl-spiro[8-azabicyclo[3.2.1]octane-3,2′-oxirane]

Disolventes

DMSO

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis slowly added
2. 2
   workup.STIRRINGThe reaction medium is kept stirring for 4 h
3. 3
   workup.STIRRINGwithout stirring for 60 h
4. 4
   Lavadothe organic phase is washed with a saturated aqueous sodium chloride solution
5. 5
   Secadodried over MgSO4
6. 6
   Otroare obtained

Procedimiento

Trimethyl sulfoxonium iodide (3.07 g, 13.9 mmol) is placed in 18 ml of DMSO under nitrogen in the presence of sodium hydride dispersed at 60% in oil (0.56 g, 13.9 mmol). After stirring for 30 min at ambient temperature, 8-benzyl-8-aza-bicyclo[3.2.1]octan-3-one (2.0 g, 9.3 mmol) solubilized in 3 ml of DMSO is slowly added. The reaction medium is kept stirring for 4 h and then kept without stirring for 60 h, After hydrolysis, and extraction with ethyl acetate, the organic phase is washed with a saturated aqueous sodium chloride solution and dried over MgSO4. 2.04 g of 8-benzyl-spiro[8-azabicyclo[3.2.1]octane-3,2′-oxirane], subsequently used as it is, are obtained.

Fuente