Реакция #64931

Уравнение реакции

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

Растворители

tetrahydrofuran

tetrahydrofuran

water

water

water

Условия реакции

Обработка

1. 1
   ТемператураThe mixture is heated
2. 2
   Температураunder reflux for 72 hours
3. 3
   Концентрированиеconcentrated
4. 4
   workup.DISSOLUTIONthe inorganic salts are dissolved in water
5. 5
   Экстракцияthe mixture is extracted with chloroform
6. 6
   СушкаThe extract is dried over potassium carbonate
7. 7
   Концентрированиеconcentrated
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
    ТемператураThe mixture is heated
11. 11
    Температураunder reflux for one hour
12. 12
    ТемператураThe mixture is subsequently heated
13. 13
    Температураunder reflux overnight
14. 14
    Концентрированиеconcentrated
15. 15
    Экстракцияthe mixture is extracted with chloroform
16. 16
    СушкаThe extract is dried over potassium carbonate
17. 17
    Концентрированиеconcentrated
18. 18
    workup.DISTILLATIONthe residue is distilled
19. 19
    Другоеare obtained
20. 20
    Температураthe mixture is heated
21. 21
    Температураunder reflux for 2 hours
22. 22
    ФильтрацияThe inorganic salts are filtered off with suction
23. 23
    Промывкаwashed several times with chloroform
24. 24
    СушкаThe organic phases are dried over potassium carbonate
25. 25
    Концентрированиеconcentrated
26. 26
    workup.DISTILLATIONthe residue is distilled

Методика

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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