反应详情

To a stirred solution of 30 ml of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise a solution of 2.2 g of 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide in 100 ml of benzene over a 30 minute period at room temperature under nitrogen atmosphere. The reaction vessel is warmed slightly to maintain solution. The clear yellow solution is then heated to reflux under nitrogen atmosphere for one hour. The solution is cooled and the excess reagent decomposed with 5 N sodium hydroxide. Water is added to the mixture and the benzene phase is separated. The aqueous phase is extracted with ether and the ether extracts are combined with the benzene phase and dried over magnesium sulfate. This organic phase is evaporated under reduced pressure to give a viscous liquid, which crystallizes to a tacky off-white solid consisting of the racemic base 1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane. This solid is dissolved in ethanol, acidified with ethanolic hydrogen chloride, and ether is added producing off-white crystals of the hydrochloride. This is recrystallized from ethanol giving off-white crystals, mp 215°-217° C.

1. temperatureThe reaction vessel is warmed slightly
2. temperatureto maintain solution
3. temperatureThe clear yellow solution is then heated
4. temperatureto reflux under nitrogen atmosphere for one hour
5. temperatureThe solution is cooled
6. customthe benzene phase is separated
7. extractionThe aqueous phase is extracted with ether
8. dry with materialdried over magnesium sulfate
9. customThis organic phase is evaporated under reduced pressure
10. customto give a viscous liquid, which
11. customcrystallizes to a tacky off-white solid
12. dissolutionThis solid is dissolved in ethanol
13. additionis added