Реакция #71880

Уравнение реакции

Ethyl bromopyruvate

sodium bicarbonate

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

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

→

title compound

Выход 79.4%

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

Выход 79.4%

Растворители

THF

Условия реакции

Обработка

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

Методика

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%).

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