反应 #953

反应方程式

triphenylphosphine

triphenylphosphine

4-(benzyloxycarbonylamidino) benzyl azide

( iii )

4-(benzyloxycarbonylamidino) benzyl azide

cyanobenzyl bromide

→

4-aminomethyl-1-(N-benzyloxycarbonylamidino)benzene

溶剂

THF

反应条件

后处理

1. 1
   其他to stand for 4 h before removal of the solvent in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
3. 3
   萃取extracted with 2M HCl
4. 4
   洗涤The aqueous phase was washed with methylene chloride and ether
5. 5
   萃取Extraction with methylene chloride
6. 6
   其他by drying
7. 7
   其他(K2CO3) and removal of the solvent in vacuo
8. 8
   其他gave 20 g (The total
9. 9
   其他yield

实验过程

26.3 g (100 mmol) triphenylphosphine was added at room temperature to the 4-(benzyloxycarbonylamidino) benzyl azide from (iii) above dissolved in 160 ml THF. After 16 h an additional 6.6 g (25 mmol) triphenylphosphine was added and the solution was allowed to stand for 4 h before removal of the solvent in vacuo. The residue was dissolved in methylene chloride and extracted with 2M HCl. The aqueous phase was washed with methylene chloride and ether and was subsequently made alcaline with 3.75M sodium hydroxide solution. Extraction with methylene chloride followed by drying (K2CO3) and removal of the solvent in vacuo gave 20 g (The total yield starting from cyanobenzyl bromide is 28%) of a yellow oil which solidified on standing.

来源