반응 #957

반응 방정식

HCl

Sodium borohydride

4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

→

4-Aminoethyl-1-benzyloxycarbonylamidino piperidine

용매

water

water

water

tetrahydrofurane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added carefully to the
2. 2
   온도cooled aqueous slurry above
3. 3
   workup.STIRRINGAfter 4 h of stirring at room temperature the mixture
4. 4
   온도cooled again
5. 5
   여과The mixture was filtered through celite
6. 6
   세척the celite was rinsed with additional water
7. 7
   기타The tetrahydrofuran was evaporated
8. 8
   세척the aqueous phase was washed with ethyl acetate
9. 9
   추출extracted with methylene chloride three times
10. 10
    세척The combined organic phase was washed with water
11. 11
    건조dried (Na2SO4)
12. 12
    기타evaporated
13. 13
    기타The product was used in the following step without further purification

실험 절차

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.

출처