Synthesis 2010(15): 2512-2514  
DOI: 10.1055/s-0029-1218823
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Short and Efficient Synthesis of (S)-(+)-2-(Hydroxymethyl)-6-piperidin-2-one

Puspesh K. Upadhyay, Pradeep Kumar*
Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25902629; e-Mail: pk.tripathi@ncl.res.in;
Further Information

Publication History

Received 1 April 2010
Publication Date:
18 June 2010 (online)

Abstract

A concise synthesis of (S)-(+)-2-(hydroxymethyl)-6-piperidin-2-one is described that employs l-aspartic acid as chiral pool starting material and Wittig reaction as the key step.

    References

  • 1a Hermitage SA. Moloney MG. Tetrahedron: Asymmetry  1994,  5:  1463 
  • 1b Davies CE. Heightman TD. Hermitage SA. Moloney MG. Synth. Commun.  1996,  26:  687 
  • 1c Ezquerra J. Pedregal C. Escribano A. Carreno MC. Ruano JLG. Tetrahedron Lett.  1995,  36:  3247 
  • 1d Huang S.-B. Nelson JS. Weller DD. Synth. Commun.  1989,  3485 
  • 2 Hanessian S. Reinhold U. Gentile G. Angew. Chem. Int. Ed.  1997,  36:  1881 
  • 3 Huang S.-B. Nelson JS. Weller DD. J. Org. Chem.  1991,  56:  6007 
  • 4 Hodgkinson TJ. Shipman M. Synthesis  1998,  1141 
  • 5a Pandey SK. Kumar P. Synlett  2007,  2894 
  • 5b Pandey SK. Kumar P. Tetrahedron Lett.  2005,  46:  4091 
  • 5c Cherian SK. Kumar P. Tetrahedron: Asymmetry  2007,  18:  982 
  • 5d Kandula SV. Kumar P. Tetrahedron  2006,  62:  9942 
  • 5e Kumar P. Bodas MS.
    J. Org. Chem.  2005,  70:  360 
  • 5f Bodas MS. Upadhyay PK. Kumar P. Tetrahedron Lett.  2004,  45:  987 
  • 5g Upadhyay PK. Prasad R. Pandey M. Kumar P. Tetrahedron Lett.  2009,  50:  2440 
  • 6a Fanning KN. Sutherland A. Tetrahedron Lett.  2007,  48:  8479 
  • 6b Padron JM. Kokotos G. Martin T. Markidis T. Gibbons WA. Martin VS. Tetrahedron: Asymmetry  1998,  9:  3381