Reacción #52610

Ecuación de reacción

4-(2-dimethylcarbamoyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

borane tetrahydrofuran

MeOH

→

4-(3-dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Rendimiento 65.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed overnight
2. 2
   Temperaturarefluxing
3. 3
   TemperaturaThe reaction mixture was cooled
4. 4
   Otroquenched with 1N HCl
5. 5
   Extracciónextracted with EtOAc
6. 6
   Extracciónextracted with EtOAc
7. 7
   ExtracciónThe EtOAc extract
8. 8
   Lavadowas washed with brine
9. 9
   Otrodried
10. 10
    Concentraciónconcentrated

Procedimiento

To a heterogeneous mixture of 4-(2-dimethylcarbamoyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (1.01 g, 4 mmol) in THF (9 mL) was added dropwise 8 mL of borane-tetrahydrofuran complex (1M in THF). The mixture was refluxed overnight. Then 9.0 mL of MeOH was added slowly to the reaction and refluxing was continued for another 2 hr. The reaction mixture was cooled, quenched with 1N HCl and extracted with EtOAc. The aqueous layer was basified with aqueous KOH and extracted with EtOAc. The EtOAc extract was washed with brine, dried and concentrated to give 616 mg (65%) of 4-(3-dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester as a faint orange oil.

Fuente