Reacción #71761

Ecuación de reacción

Methyl 3-bromobenzoate

BINAP

cesium carbonate

Example ( 40b )

Benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate

ammonium chloride

→

title compound

Rendimiento 38.6%

Methyl cis(±)-3-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

Rendimiento 38.6%

Disolventes

dioxane

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with ethyl acetate
2. 2
   LavadoThen, the organic layer was washed with brine
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThereafter, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 80/20, 0/100)

Procedimiento

Benzyl cis(±)-4-(3-methoxypiperidin-4-yl)-carbamate obtained by the method described in Example (40b) (0.5 g, 1.89 mmol) was dissolved in dioxane (20 ml) and DMF (6 mL). Methyl 3-bromobenzoate (0.35 g, 1.63 mmol), palladium acetate (39 mg, 0.17 mmol), BINAP (214 mg, 0.34 mmol) and cesium carbonate (1.35 g, 4.14 mmol) were added, and the mixture was stirred at 100° C. for 17 hours. Aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Thereafter, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 80/20, 0/100) to obtain 250.9 mg of the title compound as a yellow oily substance (39%).

Fuente