Reaction #5073

Reaction equation

sodium sulphate

Lithium aluminium hydride

2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one

sodium hydroxide

→

2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-ol

Solvents

water

Water

THF

Conditions

Workup

1. 1
   Temperaturewarmed to room temperature whereupon the reaction mixture
2. 2
   Otheraffording a granular precipitate
3. 3
   Filtrationthe mixture was filtered
4. 4
   Otherthe filtrate evaporated
5. 5
   OtherThe resulting diol was used without further purification

Procedure

2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one (210 mg) was dissolved in THF (5 ml) at -78° C. under argon. Lithium aluminium hydride (3 ml, 1.0M in ether) was added and the mixture stirred at -78° C. for 30 min, and then warmed to room temperature whereupon the reaction mixture became homogeneous. Water (0.1 ml) was added followed by sodium hydroxide (0.35 ml, 3N) and water (0.35 ml) affording a granular precipitate. Solid sodium sulphate was added, the mixture was filtered and the filtrate evaporated. The resulting diol was used without further purification.

Source