Reaktion #71880

Reaktionsgleichung

Ethyl bromopyruvate

sodium bicarbonate

cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

cis(±)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

→

title compound

Ausbeute 79.4%

Ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

Ausbeute 79.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe insoluble matter was filtered off
2. 2
   WaschenThis was washed with water and brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1, 4/1)

Vorschrift

Ethyl bromopyruvate (2.93 g, 15 mmol) and sodium bicarbonate (2.10 g, 25 mmol) were added to a solution of cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (1.4 g, 4.56 mmol) in THF (30 mL), and the mixture was stirred at 70° C. for three hours. The insoluble matter was filtered off, followed by dilution with ethyl acetate. This was washed with water and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1, 4/1) to obtain 1.46 g of the title compound as a colorless solid (79%).

Quelle