Reaktion #64931

Reaktionsgleichung

methyl iodide

3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane

dioxane

lithium aluminum hydride

lithium aluminum hydride

potassium hydroxide

sodium azide

→

trans-3-Amino-1-benzyl-4-methoxy-pyrrolidine

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

water

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturunder reflux for 72 hours
3. 3
   Einengenconcentrated
4. 4
   workup.DISSOLUTIONthe inorganic salts are dissolved in water
5. 5
   Extraktionthe mixture is extracted with chloroform
6. 6
   TrocknenThe extract is dried over potassium carbonate
7. 7
   Einengenconcentrated
8. 8
   workup.DISSOLUTIONThe residue is dissolved in 50 ml of absolute tetrahydrofuran
9. 9
   workup.ADDITIONthe solution is added dropwise to 4 g of sodium hydride (80% strength in paraffin oil) in 200 ml of absolute tetrahydrofuran
10. 10
    TemperaturThe mixture is heated
11. 11
    Temperaturunder reflux for one hour
12. 12
    TemperaturThe mixture is subsequently heated
13. 13
    Temperaturunder reflux overnight
14. 14
    Einengenconcentrated
15. 15
    Extraktionthe mixture is extracted with chloroform
16. 16
    TrocknenThe extract is dried over potassium carbonate
17. 17
    Einengenconcentrated
18. 18
    workup.DISTILLATIONthe residue is distilled
19. 19
    Sonstigeare obtained
20. 20
    Temperaturthe mixture is heated
21. 21
    Temperaturunder reflux for 2 hours
22. 22
    FiltrationThe inorganic salts are filtered off with suction
23. 23
    Waschenwashed several times with chloroform
24. 24
    TrocknenThe organic phases are dried over potassium carbonate
25. 25
    Einengenconcentrated
26. 26
    workup.DISTILLATIONthe residue is distilled

Vorschrift

27 g (0.41 mol) of sodium azide are dissolved in 50 ml of water, and 17.5 g (0.1 mol) of 3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane in 300 ml of dioxane are added. The mixture is heated under reflux for 72 hours and concentrated, the inorganic salts are dissolved in water and the mixture is extracted with chloroform. The extract is dried over potassium carbonate and concentrated. The residue is dissolved in 50 ml of absolute tetrahydrofuran and the solution is added dropwise to 4 g of sodium hydride (80% strength in paraffin oil) in 200 ml of absolute tetrahydrofuran. The mixture is heated under reflux for one hour and 15 g (0.1 mol) of methyl iodide are then added dropwise. The mixture is subsequently heated under reflux overnight and concentrated, the residue is taken up in water and the mixture is extracted with chloroform. The extract is dried over potassium carbonate and concentrated and the residue is distilled. 13.1 g of a material which is 73% pure according to the gas chromatogram are obtained. 12.7 g of this material in 40 ml of absolute tetrahydrofuran are added dropwise to a suspension of 4 g of lithium aluminum hydride in 150 ml of absolute tetrahydrofuran and the mixture is heated under reflux for 2 hours. Excess lithium aluminum hydride is decomposed by careful dropwise addition of 4 ml portions of water and 15% strength potassium hydroxide solution and again 4 ml of water. The inorganic salts are filtered off with suction and washed several times with chloroform. The organic phases are dried over potassium carbonate and concentrated and the residue is distilled.

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