Reaction #71897

Reaction equation

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

ethyl α-chloroacetoacetate

sodium bicarbonate

→

title compound

Yield 31.1%

Ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate

Yield 31.1%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with water and brine
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   Concentrationconcentration under reduced pressure
4. 4
   Otherthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 4/1)

Procedure

cis(±)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (0.92 g, 3 mmol), ethyl α-chloroacetoacetate (3.29 g, 20 mmol) and sodium bicarbonate (0.84 g, 10 mmol) were stirred at 120° C. for three hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 4/1) to obtain 0.39 g of the title compound as a light brown solid (27%).

Source