Реакция #82270

Уравнение реакции

diethyl azodicarboxylate

vanillin

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

triphenylphosphine

→

title compound

Выход 77.9%

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

Выход 77.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter concentrating
2. 2
   Другоеthe resulting reaction solution
3. 3
   Другоеthe thus obtained residue was purified

Методика

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.

Источник