반응 #43617

반응 방정식

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

수율 109.6%

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

수율 109.6%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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%).

출처