Реакция #953

Уравнение реакции

triphenylphosphine

triphenylphosphine

4-(benzyloxycarbonylamidino) benzyl azide

( iii )

4-(benzyloxycarbonylamidino) benzyl azide

cyanobenzyl bromide

→

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

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеto stand for 4 h before removal of the solvent in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
3. 3
   Экстракцияextracted with 2M HCl
4. 4
   ПромывкаThe aqueous phase was washed with methylene chloride and ether
5. 5
   ЭкстракцияExtraction with methylene chloride
6. 6
   Другоеby drying
7. 7
   Другое(K2CO3) and removal of the solvent in vacuo
8. 8
   Другоеgave 20 g (The total
9. 9
   Другоеyield

Методика

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.

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