Reacción #5075

Ecuación de reacción

2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one

Phenylmagnesium bromide

→

title compound

2-[(2-Chlorophenyl)phenylmethyl]-1-azabicyclo[2.2.2]octan-3-one

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroplaced in a dropping funnel
2. 2
   TemperaturaThis was cooled in an ice/water bath
3. 3
   OtroAfter 3 hrs the reaction was quenched with ammonium chloride solution
4. 4
   Extracciónthe aqueous layer extracted with dichloromethane (×4)
5. 5
   Secadodried (MgSO4)
6. 6
   OtroThe solvent was removed in vacuo
7. 7
   Otrothe residue purified by chromatography on silica eluting with 1:1 hexane

Procedimiento

2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one (3 g) was dissolved in toluene (30 ml) and placed in a dropping funnel. Phenylmagnesium bromide was dissolved in toluene (15 ml) and stirred under nitrogen. This was cooled in an ice/water bath and the benzylidene solution was added dropwise. After 3 hrs the reaction was quenched with ammonium chloride solution and the aqueous layer extracted with dichloromethane (×4); this was combined with the original toluene layer and dried (MgSO4). The solvent was removed in vacuo and the residue purified by chromatography on silica eluting with 1:1 hexane:diethyl ether which afforded the title compound as a 2:1 mixture of its diastereoisomers:

Fuente