반응 #953

반응 방정식

triphenylphosphine

triphenylphosphine

4-(benzyloxycarbonylamidino) benzyl azide

( iii )

4-(benzyloxycarbonylamidino) benzyl azide

cyanobenzyl bromide

→

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

용매

THF

반응 조건

후처리

1. 1
   기타to stand for 4 h before removal of the solvent in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
3. 3
   추출extracted with 2M HCl
4. 4
   세척The aqueous phase was washed with methylene chloride and ether
5. 5
   추출Extraction with methylene chloride
6. 6
   기타by drying
7. 7
   기타(K2CO3) and removal of the solvent in vacuo
8. 8
   기타gave 20 g (The total
9. 9
   기타yield

실험 절차

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.

출처