Réaction #957

Équation de réaction

HCl

Sodium borohydride

4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

→

4-Aminoethyl-1-benzyloxycarbonylamidino piperidine

Solvants

water

water

water

tetrahydrofurane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added carefully to the
2. 2
   Températurecooled aqueous slurry above
3. 3
   workup.STIRRINGAfter 4 h of stirring at room temperature the mixture
4. 4
   Températurecooled again
5. 5
   FiltrationThe mixture was filtered through celite
6. 6
   Lavagethe celite was rinsed with additional water
7. 7
   AutreThe tetrahydrofuran was evaporated
8. 8
   Lavagethe aqueous phase was washed with ethyl acetate
9. 9
   Extractionextracted with methylene chloride three times
10. 10
    LavageThe combined organic phase was washed with water
11. 11
    Séchagedried (Na2SO4)
12. 12
    Autreevaporated
13. 13
    AutreThe product was used in the following step without further purification

Mode opératoire

To 30 ml of water was added 0.40 g of 10% Pd/C. Sodium borohydride, 1.0 g (0.031 mol), was dissolved in 30 ml of water and was added carefully to the stirred and ice-cooled slurry of Pd/C and water. 4-Azidoethyl-1-benzyloxycarbonylamidino piperidine, 2.9 g (8.8 mmol), was dissolved in 80 ml of tetrahydrofurane and this solution was added dropwise to the ice-cooled aqueous slurry above. After 4 h of stirring at room temperature the mixture was ice-cooled again and 30 ml of 2M HCl was added. The mixture was filtered through celite and the celite was rinsed with additional water. The tetrahydrofuran was evaporated and the aqueous phase was washed with ethyl acetate. The aqueous phase was made alkaline with 2M NaOH and extracted with methylene chloride three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The product was used in the following step without further purification.

Source