反应详情

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:

1. customplaced in a dropping funnel
2. temperatureThis was cooled in an ice/water bath
3. customAfter 3 hrs the reaction was quenched with ammonium chloride solution
4. extractionthe aqueous layer extracted with dichloromethane (×4)
5. dry with materialdried (MgSO4)
6. customThe solvent was removed in vacuo
7. customthe residue purified by chromatography on silica eluting with 1:1 hexane