Reaktion #72102

Reaktionsgleichung

Methyl 3-bromobenzoate

BINAP

cesium carbonate

benzyl piperidin-4-yl-carbamate

Benzyl piperidin-4-yl-carbamate

→

title compound

Ausbeute 26.6%

Methyl 3-(4-benzyloxycarbonylaminopiperidin-1-yl)benzoate

Ausbeute 26.6%

Lösungsmittel

ethyl acetate

1,4-dioxane

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled
2. 2
   Waschenwashed with brine
3. 3
   TrocknenThe organic layer was dried over magnesium sulfate
4. 4
   Sonstigethe solvent was evaporated under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1)

Vorschrift

Methyl 3-bromobenzoate (230 mg, 1.07 mmol), palladium acetate (12 mg, 0.054 mmol), BINAP (133 mg, 0.214 mmol) and cesium carbonate (767 mg, 2.35 mmol) were added to a solution of benzyl piperidin-4-yl-carbamate obtained in Example (192b) (248 mg, 0.817 mmol) in 1,4-dioxane (10 mL) and N,N-dimethylformamide (2.5 mL), and the mixture was stirred at 100° C. for 20 hours. The reaction solution was cooled, diluted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1) to obtain 80 mg of the title compound as a colorless oily substance (20%).

Quelle