Reacción #453716

Ecuación de reacción

dimethylformamide

Sodium hydride

3-azabicyclo[3.1.0]hexane-2,4-dione

1-iodoheptane

→

title compound

3-n-Heptyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Disolventes

tetrahydrofuran

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for two hours at room temperature
2. 2
   workup.STIRRINGthe reaction mixture was stirred for a further 16 hours at room temperature
3. 3
   Otropartitioned with water (20 ml)
4. 4
   ExtracciónThe aqueous phase was extracted with dichloromethane (20 ml)
5. 5
   Lavadothe combined organic extracts were washed with water (2×20 ml)
6. 6
   Secadodried (MgSO4)
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe residue was purified by chromatography on silica gel (50 g)

Procedimiento

Sodium hydride (0.11 g) was added to a solution of 3-azabicyclo[3.1.0]hexane-2,4-dione (0.3 g) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere at room temperature. The suspension was stirred for 5 minutes and 1-iodoheptane (0.61 g) was then added in one portion to the reaction mixture. After stirring for two hours at room temperature, dimethylformamide (5 ml) was added and the reaction mixture was stirred for a further 16 hours at room temperature. The reaction mixture was diluted with dichloromethane and then partitioned with water (20 ml). The aqueous phase was extracted with dichloromethane (20 ml) and the combined organic extracts were washed with water (2×20 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel (50 g) using 25-30% ethyl acetate/hexane as eluant to give the title compound as a colourless oil.

Fuente