反応 #957

反応方程式

HCl

Sodium borohydride

4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

→

4-Aminoethyl-1-benzyloxycarbonylamidino piperidine

溶媒

water

water

water

tetrahydrofurane

反応条件

後処理

1. 1
   workup.ADDITIONwas added carefully to the
2. 2
   温度cooled aqueous slurry above
3. 3
   workup.STIRRINGAfter 4 h of stirring at room temperature the mixture
4. 4
   温度cooled again
5. 5
   ろ過The mixture was filtered through celite
6. 6
   洗浄the celite was rinsed with additional water
7. 7
   その他The tetrahydrofuran was evaporated
8. 8
   洗浄the aqueous phase was washed with ethyl acetate
9. 9
   抽出extracted with methylene chloride three times
10. 10
    洗浄The combined organic phase was washed with water
11. 11
    乾燥dried (Na2SO4)
12. 12
    その他evaporated
13. 13
    その他The product was used in the following step without further purification

実験手順

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.

出典