A chemoenzymatic scalable route to optically active (R)-1-(pyridin-3-yl)-2-aminoethanol, valuable moiety of beta3-adrenergic receptor agonists

Bioorg Med Chem. 2006 Feb 15;14(4):1207-14. doi: 10.1016/j.bmc.2005.09.046. Epub 2005 Oct 10.

Abstract

Enantiomerically pure (R)-2-chloro-1-(pyridin-3-yl)ethanol has been prepared by kinetic resolution performed in the presence of Candida antarctica SP435-L lipase immobilized on a macroporous polyacrylate resin (Novozym 435). It was converted into (R)-1-(pyridin-3-yl)-2-aminoethanol, left-hand side of beta(3)-adrenergic receptor ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic beta-3 Receptor Agonists*
  • Candida / enzymology
  • Enzymes, Immobilized / metabolism
  • Ethanolamines / chemical synthesis*
  • Ethanolamines / chemistry
  • Ethanolamines / pharmacology*
  • Kinetics
  • Lipase / metabolism*
  • Models, Molecular
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Receptors, Adrenergic, beta-3 / metabolism
  • Stereoisomerism

Substances

  • (R)-1-(pyridin-3-yl)-2-aminoethanol
  • Adrenergic beta-3 Receptor Agonists
  • Enzymes, Immobilized
  • Ethanolamines
  • Pyridines
  • Receptors, Adrenergic, beta-3
  • Lipase