반응 #160433

반응 방정식

1-benzylpyrrolidine-3-amine

1-Ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride

5-formyl-2,4-dimethyl-1H-pyrrole-3-formic acid

1-hydroxybenzotriazole

→

N-(1-benzylpyrrolidin-3-yl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide

수율 52.4%

용매

DMF

triethylamine

water

water

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1.5 hrs
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature until completion
3. 3
   추출the mixture was extracted with 10% methanol/dichloromethane (300 mL×3)
4. 4
   세척the combined organic phase was washed with saturated salt water (300 mL×3)
5. 5
   건조dried over anhydrous Na2SO4
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   기타The residue was then chromatographed on silica gel (eluted with methanol/ethyl acetate=1/1)

실험 절차

1-Ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (268.1 g, 1.4 mol), triethylamine (280.0 mL), 5-formyl-2,4-dimethyl-1H-pyrrole-3-formic acid (167.0 g, 1.0 mol) and 1-hydroxybenzotriazole (189.2 g, 1.4 mol) were added to DMF (500 mL) with stirring at about 0° C. and stirred for 1.5 hrs, then 1-benzylpyrrolidine-3-amine (1.2 mol) was added. The reaction was stirred at room temperature until completion was indicated by thin layer chromatography (TLC). 120 mL of water and 100 mL of saturated salt water were added, and the mixture was extracted with 10% methanol/dichloromethane (300 mL×3), the combined organic phase was washed with saturated salt water (300 mL×3), dried over anhydrous Na2SO4, and the solvent was distilled off under reduced pressure. The residue was then chromatographed on silica gel (eluted with methanol/ethyl acetate=1/1) to give 170.3 g (524 mmol) of N-(1-benzylpyrrolidin-3-yl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide as an off-white solid. Yield 52.4%.

출처