An effective new synthesis of 4-aminopyrrole-2-carboxylates.
[reaction: see text] A series of 4-amino-1H-pyrrole-2-carboxylic acid benzyl esters has been synthesized in 61-84% yields on treatment of N-PhF-4-oxoproline benzyl ester and its 3-alkyl-substituted derivatives with different primary and secondary amines and a catalytic amount of TsOH in THF. 4-Hydroxy-1H-pyrrole-2-carboxylic acid benzyl esters were prepared in 59 and 70% yields by treatment of N-PhF-4-oxoproline benzyl esters with ammonium hydroxide in THF.
Département de chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec, Canada H3C 3J7.
Félix-Antoine
FA
Marcotte
William D
WD
Lubell
D000478:Alkylation; D000588:Amines / Q000737:chemistry; D000998:Antiviral Agents / Q000737:chemistry; D001565:Benzoates; D002626:Chemistry, Pharmaceutical; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000588:Amines; D000998:Antiviral Agents; D001565:Benzoates; C047429:4-aminopyrrolidine-2-carboxylic acid; D011392:Proline