Synthesis of the enantiomers of 1-{2-hydroxy-3-[4-(2-hydroxy-phenyl)-piperazin-1-yl]-propyl}-pyrrolidin-2-one using soluble and polystyrene bound salenCo(III)OAc complexes as catalysts of hydrolytic kinetic resolution

The asymmetric synthesis of 1-{2-hydroxy-3-[4-(2-hydroxy-phenyl)-piperazin-1-yl]propyl}-pyrrolidin-2-one 3 is described. Enantiomers of compound 3 were synthesized by hydrolytic kinetic resolution (HKR) of racemic 1-oxiranylmethyl-pyrrolidin-2-one rac-2 using soluble or polystyrene bound salenCo(III...

Full description

Saved in:
Bibliographic Details
Published inPolish journal of chemistry Vol. 81; no. 2; pp. 179 - 186
Main Authors Kulig, K., Nowicki, P., Malawska, B.
Format Journal Article
LanguageEnglish
Published WARSAW Polish Chemical Soc 01.02.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
aminoalcohols
asymmetric synthesis
polymer supported catalysis
DERIVATIVES
Online AccessGet more information

Cover

More Information
Summary:The asymmetric synthesis of 1-{2-hydroxy-3-[4-(2-hydroxy-phenyl)-piperazin-1-yl]propyl}-pyrrolidin-2-one 3 is described. Enantiomers of compound 3 were synthesized by hydrolytic kinetic resolution (HKR) of racemic 1-oxiranylmethyl-pyrrolidin-2-one rac-2 using soluble or polystyrene bound salenCo(III)OAc complexes folowing its aminolysis with 1-(2-hydroxy-phenyl)-piperazine. The enantiomeric purity of obtained dihydrochloride salts of compounds 3 was determined by HPLC method with Chiralpack IA column. The cc's determined for enantiomers of compound 3 were in range 92-96% and indicated that proposed methods are effective tools for the synthesis of aminoalcohols. The application of polystyrene bound catalyst of HKR enables its easy isolation from reaction mixture and recovery.
ISSN:0137-5083