反応 #43617

反応方程式

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

収率 109.6%

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

収率 109.6%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他The solvent was then removed under reduced pressure
2. 2
   workup.ADDITIONthe residue was treated with aqueous sodium bicarbonate solution
3. 3
   抽出The aqueous phase was extracted with 9:1 dichloromethane
4. 4
   乾燥The organic layer was dried (MgSO4)
5. 5
   その他the solvent was removed under reduced pressure

実験手順

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%).

出典