Reacción #82943

Ecuación de reacción

sodium boron hydride

α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride

2,3-dimethoxybenzaldehyde

triethylamine

→

3,4-dimethoxybenzyl alcohol

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONafter adding
2. 2
   TemperaturaThe mixture was heated
3. 3
   Temperaturaunder reflux for 30 minutes
4. 4
   workup.STIRRINGwhile stirring under ice cooling
5. 5
   Concentraciónthe mixture was concentrated
6. 6
   Otrothe chloroform layer was collected
7. 7
   Lavadowashed with water
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off
10. 10
    Otrothe residue was recrystallized from ethyl acetate-n-hexane

Procedimiento

1.0 g of α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride was suspended in 5 ml of methanol, and after adding thereto 0.85 g of 2,3-dimethoxybenzaldehyde, 0.63 ml of triethylamine was added dropwise to the mixture while stirring at room temperature. The mixture was heated under reflux for 30 minutes, and 0.24 g of sodium boron hydride was added slowly to the mixture while stirring under ice cooling. After the foaming stopped, the mixture was concentrated. The residue was subjected to a separating procedure with chloroform and water, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 1.07 g of α-[[2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 96°-97° C.

Fuente