A practical synthesis of the major 3-hydroxy-2-pyrrolidinone metabolite of a potent CDK2/cyclin A inhibitor

  • Bioorg Med Chem Lett. 2006 Jun 15;16(12):3205-8. doi: 10.1016/j.bmcl.2006.03.051.
Marcella Nesi  1 ,  Daniela Borghi ,  Maria Gabriella Brasca ,  Francesco Fiorentini ,  Paolo Pevarello
Affiliations
  • 1. Department of Chemistry, Oncology Business Unit, Nerviano Medical Sciences, Viale Pasteur 10-20014 Nerviano, MI, Italy. [email protected]
PMID: 16616492 DOI: 10.1016/j.bmcl.2006.03.051
Abstract

The synthesis of the major metabolite of a potent 3-aminopyrazole CDK2/cyclin A inhibitor is presented. A stereoconservative approach starting from malic acid was employed to construct the hydroxy-substituted pyrrolidinone moiety. In the key step of the synthesis the use of cyanoborohydride immobilized on Amberlyst 26 in trifluoroethanol represented a valid alternative to conventional solution-phase reducing agents.