反应 #5069

反应方程式

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

溶剂

water

Water

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwere added dropwise to the solution
2. 2
   其他resulting in precipitation of the inorganic salts
3. 3
   过滤the mixture filtered through celite
4. 4
   其他The solvent was removed in vacuo
5. 5
   其他the residue was recrystallised from isopropanol affording the pure cis isomer
6. 6
   浓缩The mother liquors were concentrated

实验过程

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.

来源