Réaction #82270

Équation de réaction

diethyl azodicarboxylate

vanillin

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

triphenylphosphine

→

title compound

Rendement 77.9%

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

Rendement 77.9%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   ConcentrationAfter concentrating
2. 2
   Autrethe resulting reaction solution
3. 3
   Autrethe thus obtained residue was purified

Mode opératoire

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.

Source