반응 #5069

반응 방정식

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

용매

water

Water

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwere added dropwise to the solution
2. 2
   기타resulting in precipitation of the inorganic salts
3. 3
   여과the mixture filtered through celite
4. 4
   기타The solvent was removed in vacuo
5. 5
   기타the residue was recrystallised from isopropanol affording the pure cis isomer
6. 6
   농축The mother liquors were concentrated

실험 절차

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.

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