반응 #82270

반응 방정식

diethyl azodicarboxylate

vanillin

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

triphenylphosphine

→

title compound

수율 77.9%

4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-3-methoxybenzaldehyde

수율 77.9%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축After concentrating
2. 2
   기타the resulting reaction solution
3. 3
   기타the thus obtained residue was purified

실험 절차

In 50 ml of tetrahydrofuran were dissolved 3.04 g of vanillin, 3.74 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine and 5.24 g of triphenylphosphine. The thus prepared solution was mixed with 4.00 g of diethyl azodicarboxylate, and the mixture was stirred at room temperature for 18 hours. After concentrating the resulting reaction solution, the thus obtained residue was purified by subjecting it to silica gel column chromatography using an ethanol/chloroform mixture as an elution solvent. In this way, 5.0 g of the title compound was obtained in an oily form.

출처