Reaction #957

Reaction equation

HCl

Sodium borohydride

4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

→

4-Aminoethyl-1-benzyloxycarbonylamidino piperidine

Solvents

water

water

water

tetrahydrofurane

Conditions

Workup

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

Procedure

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