反应 #64929

反应方程式

phthalimide

diethyl azodicarboxylate

trans-1-benzyl-3-hydroxy-4-methoxypyrrolidine

triphenylphosphine

→

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

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   浓缩concentrated
2. 2
   workup.DISSOLUTIONThe residue is dissolved in 80 ml of ethyl acetate
3. 3
   workup.ADDITION80 ml of petroleum ether are added
4. 4
   workup.WAITThe mixture is left
5. 5
   其他to crystallize out overnight
6. 6
   过滤the crystals (triphenylphosphine oxide and diethyl hydrazine-dicarboxylate) are filtered off
7. 7
   浓缩The filtrate is concentrated
8. 8
   温度the residue is heated
9. 9
   温度under reflux with 60 ml of concentrated hydrochloric acid overnight
10. 10
    其他The undissolved residues are decanted
11. 11
    浓缩the solution is concentrated
12. 12
    萃取extracted five times with 50 ml of chloroform
13. 13
    干燥The extract is dried over potassium carbonate
14. 14
    浓缩concentrated
15. 15
    workup.DISTILLATIONthe residue is distilled

实验过程

5.6 g (25 mmol) of trans-1-benzyl-3-hydroxy-4-methoxypyrrolidine and 8.6 g (33 mmol) of triphenylphosphine are initially introduced into 40 ml of absolute tetrahydrofuran and a solution of 6 g (34 mmol) of diethyl azodicarboxylate in 40 ml of absolute tetrahydrofuran is added dropwise at 0° C. 3.9 g (27 mmol) of phthalimide are then added in small portions at 0° C. in the course of one hour. The mixture is stirred at room temperature overnight and concentrated. The residue is dissolved in 80 ml of ethyl acetate and 80 ml of petroleum ether are added. The mixture is left to crystallize out overnight and the crystals (triphenylphosphine oxide and diethyl hydrazine-dicarboxylate) are filtered off. The filtrate is concentrated and the residue is heated under reflux with 60 ml of concentrated hydrochloric acid overnight. The undissolved residues are decanted and the solution is concentrated. The residue is taken up in a little water and the solution is rendered alkaline with solid potassium carbonate and extracted five times with 50 ml of chloroform. The extract is dried over potassium carbonate and concentrated and the residue is distilled.

来源