تفاعل #552140

معادلة التفاعل

carbonyl diimidazole

5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid

2,2,2-triflouroethylamine hydrochloride

1,8-diazabicyclo[5.4.0]undec-7-ene

→

5-oxo-1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinecarboxamide

المردود 28.3%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat room temperature for 30 minutes
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature overnight
3. 3
   أخرىThe solvent was removed at reduced pressure
4. 4
   غسيلwashed with 3×150 ml saturated sodium bicarbonate
5. 5
   تجفيفThe organic layer was dried over magnesium sulfate
6. 6
   أخرىthe solvent removed under reduced pressure
7. 7
   أخرىThe product was purified by column chromatography on silica with ethyl acetate

الإجراء التجريبي

A mixture of 21.9 g (0.100 mole) 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid in 150 ml tetrahydrofuran, was cooled to 0° C. in an ice bath under nitrogen and 24.32 g (0.150 mole) carbonyl diimidazole was added. The reaction was stirred at 0° C. for 30 minutes, then at room temperature for 30 minutes. A solution of 13.55 g (0.100 mole) of 2,2,2-triflouroethylamine hydrochloride, 15.22 g (0.100 mole) 1,8-diazabicyclo[5.4.0]undec-7-ene and 100 ml tetrahydrofuran was added. The reaction was stirred at room temperature overnight. The solvent was removed at reduced pressure. The residue was taken up in dichloromethane and washed with 3×150 ml saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and the solvent removed under reduced pressure. The product was purified by column chromatography on silica with ethyl acetate to give 8.50 g of 5-oxo-1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinecarboxamide, mp 110°-112° C.

المصدر