Reacción #49643

Ecuación de reacción

dihydrocinnamaldehyde

nitromethane

tetramethylguanidine

→

(D,L)-4-phenyl-2-hydroxy-1-butylamine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónIt is concentrated in vacuo
2. 2
   workup.ADDITION5 ml of glacial acetic acid, 10 g of activated Raney nickel are added
3. 3
   workup.WAITthe mixture is then hydrogenated at 50° C. and under 25 bar H2 pressure for 5 h
4. 4
   FiltraciónThe catalyst is then filtered off
5. 5
   Concentraciónthe filtrate is concentrated in vacuo
6. 6
   Otronon-polar impurities are removed by extraction with diethyl ether
7. 7
   ExtracciónExtraction 3 times with tetrahydrofuran
8. 8
   Secadodrying over sodium sulfate, and concentration in vacuo

Procedimiento

6.70 g of dihydrocinnamaldehyde are dissolved in 20 ml of anhydrous ethanol, and 10 ml of nitromethane and 1 ml of tetramethylguanidine are added, and the mixture is stirred at RT for 1 h. It is concentrated in vacuo, the residue is taken up in 200 ml of ethanol and 5 ml of glacial acetic acid, 10 g of activated Raney nickel are added and the mixture is then hydrogenated at 50° C. and under 25 bar H2 pressure for 5 h. The catalyst is then filtered off, the filtrate is concentrated in vacuo, the residue is taken up in saturated aqueous sodium bicarbonate solution, and non-polar impurities are removed by extraction with diethyl ether. Extraction 3 times with tetrahydrofuran, drying over sodium sulfate, and concentration in vacuo provides 5.75 g of (D,L)-4-phenyl-2-hydroxy-1-butylamine as a colorless oil.

Fuente