Reacción #71880

Ecuación de reacción

Ethyl bromopyruvate

sodium bicarbonate

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

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

→

title compound

Rendimiento 79.4%

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

Rendimiento 79.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente