Synthesis 2005(6): 1028-1029  
DOI: 10.1055/s-2004-834856
PSP
© Georg Thieme Verlag Stuttgart · New York

A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor

Detlef Kampmanna, Georg Stuhlmüllera, Roger Simonb, Fabrice Cottetb, Frédéric Lerouxb, Manfred Schlosser*b
a Clariant Acetyl Building Blocks, 86368 Gersthofen, Germany
b Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale, BCh, 1015 Lausanne, Switzerland
Fax: +41(21)6939365; e-Mail: [email protected]epfl.ch;
Further Information

Publication History

Received 15 June 2004
Publication Date:
21 October 2004 (online)

Abstract

Wolff-Kishner-Huang reduction of the cheap 2,2,6,6-tetramethyl-4-piperidinone (2) provides the expensive 2,2,6,6-tetramethylpiperidine (1), the precursor to lithium 2,2,6,6-tetramethylpiperidide, in high yield. As specified in the detailed protocol, the reaction can be conveniently carried out on a >10 mol laboratory scale.

    References

  • 1 Olofson RA. Dougherty CM. J. Am. Chem. Soc.  1973,  95:  582-584  
  • 2 Smith AB. Richmond RE. J. Org. Chem.  1981,  46:  4814-4816  
  • 3 Krizan TD. Martin JC. J. Am. Chem. Soc.  1983,  105:  6155-6157  
  • 4 Crump SL. Netka J. Rickborn B. J. Org. Chem.  1985,  50:  2746-2750  
  • 5 Cuevas J.-C. Patil P. Snieckus V. Tetrahedron Lett.  1989,  30:  5841-5844  
  • 6 Faigl F. Marzi E. Schlosser M. Chem. Eur. J.  2000,  6:  771-777  
  • 7 Kopka IE. Fataftah ZA. Ratke MW. J. Org. Chem.  1987,  52:  448-450  
  • 8 Orther L. Liebigs Ann. Chem.  1928,  459:  217-233   (especially p 223)
  • 9 Kampmann D, and Stuhlmüller G. inventors; Hoechst AG, Frankfurt, Eur. Pat. Appl.  EP 661265 A1.  1995; Chem. Abstr. 1995, 123, 55713
  • 10 Rozantsev EG. Sholle VD. Synthesis  1971,  190-202  
  • 11 Rozantsev EG. Sholle VD. Synthesis  1971,  401-414  
  • 12 Keana JFW. Chem. Rev.  1978,  78:  37-64  
  • 13 Ma Z. Bobbitt JM. J. Org. Chem.  1991,  56:  6110-6114  
  • 14 Anelli PL. Biffi C. Montaneri F. Quici S. J. Org. Chem.  1987,  52:  2559-2562  
  • 15 Anelli PL. Montanari F. Quici S. Org. Synth.  1990,  69:  212-219  
  • 16 Leonard NJ. Nommensen EW. J. Am. Chem. Soc.  1949,  71:  2808-2813