تفاعل #82258

معادلة التفاعل

ethyl 4-mercaptophenylacetate

(3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine

triphenylphosphine

diethyl azodicarboxylate

→

ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)thio]phenyl]acetate

المردود 18.6%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe thus prepared mixture was stirred at room temperature for 18 hours
2. 2
   workup.DISTILLATIONAfter distilling off the solvent
3. 3
   أخرىthe resulting residue was purified

الإجراء التجريبي

20.2 g of ethyl 4-mercaptophenylacetate was dissolved in 450 ml of tetrahydrofuran. With ice cooling and with stirring, 21.0 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine, 29.4 g of triphenylphosphine and 19.5 g of diethyl azodicarboxylate were added to the above solution. The thus prepared mixture was stirred at room temperature for 18 hours. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a n-hexane/ethyl acetate mixture as an elution solvent, thereby obtaining 7.0 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)thio]phenyl]acetate.

المصدر