Реакция #43617

Уравнение реакции

ammonium bicarbonate

(cis)-4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxylic acid sodium salt

1-hydroxy-7-azabenzotriazole

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride

→

desired compound

Выход 109.6%

(cis)-4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxamide

Выход 109.6%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was then removed under reduced pressure
2. 2
   workup.ADDITIONthe residue was treated with aqueous sodium bicarbonate solution
3. 3
   ЭкстракцияThe aqueous phase was extracted with 9:1 dichloromethane
4. 4
   СушкаThe organic layer was dried (MgSO4)
5. 5
   Другоеthe solvent was removed under reduced pressure

Методика

To a solution of (cis)-4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxylic acid sodium salt (17 g) and 1-hydroxy-7-azabenzotriazole (5 g, 37 mmol) in N,N-dimethylformamide was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (14.1 g, 73.4 mmol), followed by ammonium bicarbonate (21 g, 26.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was then removed under reduced pressure and the residue was treated with aqueous sodium bicarbonate solution. The aqueous phase was extracted with 9:1 dichloromethane:methanol mixture. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a methanol and dichloromethane gradient (0-20% methanol/dichloromethane). This provided the desired compound (9.5 g, 62%).

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