Reacción #1705142

Ecuación de reacción

(R)-3-[4-(3-methoxy-azetidin-1-yl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

(E,R)-3-[4-(3-M ethoxy-azetidin-1-yl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

hydrochloric acid

ammonium chloride

sodium hydrogencarbonate

→

title compound

Rendimiento 89.0%

(R)-3-[4-(3-Chloro-2-methoxy-propylamino)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

Rendimiento 89.0%

Disolventes

Ethyl acetate

1,4-dioxane

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe phases were separated
2. 2
   Extracciónthe inorganic one was extracted with ethyl acetate (2×)
3. 3
   LavadoThe combined organic layers were washed with brine
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by flash chromatography on silica gel (25% to 100% ethyl acetate in n-heptane)

Procedimiento

To a solution of (R)-3-[4-(3-methoxy-azetidin-1-yl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime (example 270, 31 mg) in 1,4-dioxane (2 mL) was added at room temperature hydrochloric acid 4 M in 1,4-dioxane (187 μL). The reaction mixture was heated at 50° C. and stirred for 4 hours. A saturated solution of sodium hydrogencarbonate (2 mL) was added to neutralized the crude solution followed by a saturated aq. ammonium chloride solution. Ethyl acetate was added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (25% to 100% ethyl acetate in n-heptane) to yield the title compound as a light yellow foam (89%), MS (ESI+): m/z=452.3 ([M+H]+).

Fuente