Reacción #567377

Ecuación de reacción

(2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

ammonium acetate

sodium cyanoborohydride

→

title compound

Rendimiento 99.1%

(2R,5S)-2-(2-Aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Rendimiento 99.1%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with concentrated hydrochloric acid
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in water and basified with aqueous 3N NaOH (pH>10)
4. 4
   ExtracciónThe product was extracted with dichloromethane (2×) and ethyl acetate (2×)
5. 5
   SecadoThe combined organics were dried over magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (1.86 g, 4.44 mmol) in MeOH (20 mL) was added ammonium acetate (3.42 g, 44 mmol) and sodium cyanoborohydride (0.195 g, 3.1 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was quenched with concentrated hydrochloric acid and concentrated in vacuo. The residue was dissolved in water and basified with aqueous 3N NaOH (pH>10). The product was extracted with dichloromethane (2×) and ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.29 g, 69% yield)

Fuente