Reaction #94556

Reaction equation

3-(p-chlorobenzoyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane

sodium bis(2-methoxyethoxy)aluminum hydride

→

3-(p-Chlorobenzyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane

Solvents

benzene

Conditions

Workup

1. 1
   TemperatureThe mixture is refluxed for 2 hours
2. 2
   Temperaturecooled
3. 3
   Otherquenched slowly with 10N sodium hydroxide
4. 4
   workup.ADDITIONWater is added
5. 5
   Otherthe organic layer is separated
6. 6
   Washwashed 3 times with water
7. 7
   Dryingdried over sodium magnesium sulfate
8. 8
   OtherRemoval of the solvent
9. 9
   Otheryields an off-white solid, mp 88°-92° C.

Procedure

A 16.60 g portion of 3-(p-chlorobenzoyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane (prepared above) is dissolved in 160 ml of benzene and 55.5 g of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise. The mixture is refluxed for 2 hours, cooled and quenched slowly with 10N sodium hydroxide. Water is added, the organic layer is separated and washed 3 times with water and then dried over sodium magnesium sulfate. Removal of the solvent yields an off-white solid, mp 88°-92° C.

Source