反应 #640585

反应方程式

Methanol

3-Hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide

tetrahydrofuran borane tetrahydrofuran

→

3-(2-nitrobenzylamino)-1-phenylpropanol

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the dropwise addition
3. 3
   其他was returned to room temperature
4. 4
   温度heated
5. 5
   温度to reflux for six hours
6. 6
   温度to cool
7. 7
   温度under ice cooled condition and heated
8. 8
   温度to reflux for 30 minutes
9. 9
   温度to cool
10. 10
    其他the solvent was evaporated
11. 11
    workup.ADDITION0.5 N hydrochloric acid water (30 ml) was added
12. 12
    萃取After extracted with diethyl ether
13. 13
    萃取extracted with ethyl acetate
14. 14
    干燥The organic layer was dried over anhydrous sodium sulfate
15. 15
    其他the solvent was evaporated under reduced pressure

实验过程

3-Hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide (3.19 g, 10.6 mmol) was dissolved in tetrahydrofuran (50 ml) and under ice cooled condition, 1 M tetrahydrofuran-borane tetrahydrofuran solution (27.0 ml, 27.0 mmol) was added dropwise thereto. After the dropwise addition was finished, the reaction mixture was returned to room temperature and stirred for one hour, then heated to reflux for six hours and allowed to cool. Methanol (30 ml) was added thereto under ice cooled condition and heated to reflux for 30 minutes. After allowed to cool, the solvent was evaporated and 0.5 N hydrochloric acid water (30 ml) was added. After extracted with diethyl ether, the aqueous layer was adjusted to pH 8 with a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 3-(2-nitrobenzylamino)-1-phenylpropanol.

来源