Reaction #640585

Reaction equation

Methanol

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

tetrahydrofuran borane tetrahydrofuran

→

3-(2-nitrobenzylamino)-1-phenylpropanol

Solvents

tetrahydrofuran

Conditions

Workup

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

Procedure

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.

Source