Reacción #1909782

Ecuación de reacción

Water

1-tert-butoxycarbonylisonipecotic acid ethyl ester

lithium diisopropyl-amide

Ethyl iodide

→

title compound

Rendimiento 92.0%

1-tert-Butoxycarbonyl-4-ethylisonipecotic acid ethyl ester

Rendimiento 92.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 18 hours
2. 2
   Extracciónthe mixture was extracted with ethyl acetate
3. 3
   LavadoThe organic layer was washed successively with 1N hydrochloric acid, water and saturated brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   ConcentraciónThe organic layer was concentrated under reduced pressure

Procedimiento

To a solution of 1-tert-butoxycarbonylisonipecotic acid ethyl ester (576 mg) in THF (15 ml) was added a solution of lithium diisopropyl-amide (290 mg) in THF (10 ml) in a stream of argon gas at −78° C., and the reaction mixture was stirred at the same temperature for 1 hour. Ethyl iodide (0.36 ml) was added to the above solution at −78° C., and the mixture was stirred for 18 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give the title compound (585 mg, yield 92%).

Fuente