K. Kulig, P. Nowicki, B. Malawska
Jul 10, 2007
Citations
0
Influential Citations
2
Citations
Journal
ChemInform
Abstract
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 l-oxiranylmethyl-pyrrolidin-2-one rac-2 using soluble or polystyrene bound salenCo(III)OAc complexes folowing its aminolysis with l-(2-hydroxy-phenyl)-piperazine. The enantiomeric purity of obtained dihydrochloride salts of compounds 3 was determined by HPLC method with Chiralpack IA column. The ee'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.