反応 #71880

反応方程式

Ethyl bromopyruvate

sodium bicarbonate

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

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

→

title compound

収率 79.4%

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

収率 79.4%

溶媒

THF

反応条件

後処理

1. 1
   ろ過The insoluble matter was filtered off
2. 2
   洗浄This was washed with water and brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他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)

実験手順

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%).

出典