Synthesis of Methyl N-Boc-(2S,4R)-4-methylpipecolate

J Org Chem. 2010 Dec 17;75(24):8728-31. doi: 10.1021/jo102038q. Epub 2010 Nov 23.

Abstract

An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Cyclization
  • Hydrogenation
  • Molecular Structure
  • Pipecolic Acids / chemical synthesis*
  • Pipecolic Acids / chemistry
  • Stereoisomerism

Substances

  • (2S,4R)-4-methylpipecolic acid
  • Pipecolic Acids
  • pipecolic acid