Réaction #43617

Équation de réaction

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

Rendement 109.6%

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

Rendement 109.6%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source