反応 #64929

反応方程式

phthalimide

diethyl azodicarboxylate

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

triphenylphosphine

→

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

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   濃縮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
   その他to crystallize out overnight
6. 6
   ろ過the crystals (triphenylphosphine oxide and diethyl hydrazine-dicarboxylate) are filtered off
7. 7
   濃縮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
    その他The undissolved residues are decanted
11. 11
    濃縮the solution is concentrated
12. 12
    抽出extracted five times with 50 ml of chloroform
13. 13
    乾燥The extract is dried over potassium carbonate
14. 14
    濃縮concentrated
15. 15
    workup.DISTILLATIONthe residue is distilled

実験手順

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.

出典