Reacción #1364418

Ecuación de reacción

p-nitrobenzaldehyde

sarcosine methyl ester hydrochloride

water

triethylamine

→

N-(4-nitrobenzyl)sarcosine methyl ester

Rendimiento 80.2%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONto the mixture was added, under ice-
2. 2
   Temperaturacooling
3. 3
   Concentraciónthe mixture was concentrated
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with water and brine
6. 6
   Secadodried with anhydrous magnesium sulfate
7. 7
   OtroUnder reduced pressure, the solvent was evaporated
8. 8
   Otrothe residue was purified with silica gel column (ethyl acetate/hexane)

Procedimiento

In 1,2-dichloroethane (50 ml) were suspended p-nitrobenzaldehyde (5 g), sarcosine methyl ester hydrochloride (4.6 g) and triethylamine (4.6 ml), and to the mixture was added, under ice-cooling, triacetoxy sodium boron hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours. To the mixture was added water, and the mixture was concentrated, neutralized with sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give N-(4-nitrobenzyl)sarcosine methyl ester (6.3 g) as colorless oil.

Fuente