反応 #5069

反応方程式

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

溶媒

water

Water

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典