Reaktion #640585

Reaktionsgleichung

Methanol

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

tetrahydrofuran borane tetrahydrofuran

→

3-(2-nitrobenzylamino)-1-phenylpropanol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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