Reaktion #72055

Reaktionsgleichung

Potassium carbonate

methyl iodide

cis(±)-6-(4-{[(Benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyrimidine-4-carboxylic acid

Potassium carbonate

methyl iodide

→

title compound

Ausbeute 25.7%

Methyl cis(±)-6-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyrimidine-4-carboxylate

Ausbeute 25.7%

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   Waschenwashed with water and brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentration under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=40/1, 20/1, 10/1)

Vorschrift

cis(±)-6-(4-{[(Benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyrimidine-4-carboxylic acid obtained in Example (174b) (420 mg, 1.09 mmol) was dissolved in DMF (10 mL). Potassium carbonate (180 mg, 1.3 mmol) and methyl iodide (185 mg, 1.3 mmol) were added, and the mixture was stirred at room temperature overnight. Potassium carbonate (180 mg, 1.3 mmol) and methyl iodide (185 mg, 1.3 mmol) were further added, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=40/1, 20/1, 10/1) to obtain 112 mg of the title compound as a brown oily substance (26%).

Quelle