반응 #640585

반응 방정식

Methanol

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

tetrahydrofuran borane tetrahydrofuran

→

3-(2-nitrobenzylamino)-1-phenylpropanol

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

출처