Réaction #5069

Équation de réaction

Magnesium sulfate

Lithium aluminium hydride

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

sodium hydroxide

→

2-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-ol

Solvants

water

Water

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added dropwise to the solution
2. 2
   Autreresulting in precipitation of the inorganic salts
3. 3
   Filtrationthe mixture filtered through celite
4. 4
   AutreThe solvent was removed in vacuo
5. 5
   Autrethe residue was recrystallised from isopropanol affording the pure cis isomer
6. 6
   ConcentrationThe mother liquors were concentrated

Mode opératoire

2-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-one (18.9 g) was dissolved in tetrahydrofuran (350 ml), anhydrous) and cooled to -65° C. under nitrogen. Lithium aluminium hydride (1.0 M solution in THF, 40 ml) was added dropwise to the solution which was stirred at room temperature overnight. Water (2 ml) followed by sodium hydroxide (15% 2 ml) and water (6 ml) were added dropwise to the solution resulting in precipitation of the inorganic salts. Magnesium sulfate (2 g) was added and the mixture filtered through celite. The solvent was removed in vacuo and the residue was recrystallised from isopropanol affording the pure cis isomer. The mother liquors were concentrated and found to be 80:20 cis/trans by 1H NMR; this was used in the examples without further purification.

Source