Reaction #71894

Reaction equation

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

butyl 3-bromo-2-oxobutanoate

Butyl 3-bromo-2-oxobutanoate

sodium bicarbonate

→

title compound

Yield 78.2%

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

Yield 78.2%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1)

Procedure

The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (1.97 g, 6.4 mmol), butyl 3-bromo-2-oxobutanoate obtained in Example (106a) (10 g, 42.3 mmol), sodium bicarbonate (1.26 g, 15 mmol) and THF (40 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1) to obtain 2.09 g of the title compound as a yellow oily substance (73%).

Source