Reaktion #71761

Reaktionsgleichung

Methyl 3-bromobenzoate

BINAP

cesium carbonate

Example ( 40b )

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

ammonium chloride

→

title compound

Ausbeute 38.6%

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

Ausbeute 38.6%

Lösungsmittel

dioxane

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle