Reacción #350782

Ecuación de reacción

methylamine

2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole

methanol

sodium boron hydride

→

2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethyl-phenyl)thiazole

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwith stirring under ice-
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
4. 4
   OtroThe solvent was removed from the reaction mixture by distillation
5. 5
   workup.ADDITIONThe residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation
6. 6
   LavadoThe organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution
7. 7
   Otrodried
8. 8
   workup.DISTILLATIONsubjected to distillation
9. 9
   Otroto remove the solvent

Procedimiento

In 30 ml of methanol was dissolved 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole. Thereto was added 3 ml of a 30% methylamine solution. The mixture was stirred at room temperature for 14 hours and at 70° C. for 1 hour. Thereto was added 530 ml of sodium boron hydride with stirring under ice- cooling. The mixture was stirred at room temperature for 3 hours. The solvent was removed from the reaction mixture by distillation. The residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation was conducted. The organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was subjected to silica gel chromatography (eluent: dichloromethane/methanol =49/1 by v/v). From the eluate was obtained 150 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethyl-phenyl)thiazole.

Fuente