Synthesis 2010(21): 3596-3601  
DOI: 10.1055/s-0030-1258295
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Practical Synthesis of Optically Pure Menthylamines Starting from Racemic Neomenthol

Nina Welschoffa, Siegfried R. Waldvogel*a,b
a Kekulé Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
b Institute for Organic Chemistry, Johannes-Gutenberg University Mainz, Duesberg 10-24, 55128 Mainz, Germany
Fax: +49(6131)3926777; e-Mail: [email protected];
Further Information

Publication History

Received 20 August 2010
Publication Date:
13 October 2010 (online)

Abstract

A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.

    References

  • 1 Schopohl MC. Siering C. Kataeva O. Waldvogel SR. Angew. Chem. Int. Ed.  2003,  42:  2620 ; Angew. Chem. 2003, 115, 2724
  • 2 Siering C. Grimme S. Waldvogel SR. Chem. Eur. J.  2005,  11:  1877 
  • 3 Schopohl MC. Faust A. Mirk D. Fröhlich R. Kataeva O. Waldvogel SR. Eur. J. Org. Chem.  2005,  2987 
  • 4 Bomkamp M. Siering C. Landrock K. Stephan H. Fröhlich R. Waldvogel SR. Chem. Eur. J.  2007,  13:  3724 
  • 5 Schade W. Bohling C. Hohmann K. Bauer C. Orghici R. Waldvogel SR. Scheel D. Photonic Int.  2007,  1:  32 ; Photonik 2006, 38, 70
  • 6 Orghici R. Willer U. Gierszewska M. Waldvogel SR. Schade W. Appl. Phys. B  2008,  90:  355 
  • 7 Börner S. Orghici R. Waldvogel SR. Willer U. Schade W. Appl. Opt.  2009,  48:  B183 
  • 8 Schwartz U, Großer R, Piejko K.-E, Bömer B, and Arlt D. inventors; German Patent  DE3532356A1.  1987; Chem. Abstr. 1987, 107, 40614
  • 9 Grose-Bley M, Bömer B, Großer R, Arlt D, and Lange W. inventors; German Patent  DE4120695.  1992; Chem. Abstr. 1993, 119, 139964
  • 10 Bömer B, Großer R, Lange W, Zweering U, Köhler B, Sirges W, and Grose-Bley M. inventors;  DE19546136A1.  1997; Chem. Abstr. 1997, 127, 96037
  • 11 Lange W, Grosser R, Köhler B, Michel S, Bömer B, and Zweering U. inventors;  DE19714343A1.  1998; Chem. Abstr. 1998, 129, 290016
  • 12 Looft J, Vössing T, Ley J, Backes M, and Blings M. inventors; European Patent  EP1989944A1.  2008; Chem. Abstr. 2008, 149, 532086
  • 13 Shimizu T. Ohzeki T. Hiramoto K. Hori N. Nakata T. Synthesis  1999,  1373 
  • 14 Albrecht S. Defoin A. Tarnus C. Synthesis  2006,  1635 
  • 15 Nakatsuji H. Ueno K. Misaki T. Tanabe Y. Org. Lett.  2008,  10:  2131 
  • 16 Jumaryatno P. Rands-Trevor K. Blanchfield JT. Garson MJ. ARKIVOC  2007,  (vii):  157 
  • 17 Bartoli G. Di Antonio G. Giovannini R. Giuli S. Lanari S. Paoletti M. Marcantoni E. J. Org. Chem.  2008,  73:  1919 
  • 18 Viaud MC. Rollin P. Synthesis  1990,  130 
  • 19 Gansäuer A. Narayan S. Schiffer-Ndene N. Bluhm H. Oltra JE. Cuerva JM. Rosales A. Nieger M.
    J. Organomet. Chem.  2006,  691:  2327 
  • 20 Papeo G. Posteri H. Vianello P. Varasi M. Synthesis  2004,  2886 
  • 21 Wallach O. Ber. Dtsch. Chem. Ges.  1891,  24:  3992 
  • 22 Wallach O. Kuthe M. Ber. Dtsch. Chem. Ges.  1892,  25:  3313 
  • 23 Wallach O. Kuthe M. Liebigs Ann. Chem.  1893,  276:  296 
  • 24 Kulisch J. inventors; Ph.D. Thesis; University of Bonn:  Germany.  2010
  • 25 Feltkamp H. Kranklin NC. Koch F. Thanh TN. Liebigs Ann. Chem.  1967,  707:  78 
  • 26 Schopohl MC. Bergander K. Kataeva O. Fröhlich R. Waldvogel SR. Synthesis  2003,  2689 
  • 27 Griesbach U, Waldvogel SR, Kulisch J, and Malkowsky IM. inventors; Patent  WO2008003620.  2008; Chem. Abstr. 2008, 148, 154171
  • 28 Kuhn W, Funk HU, Senft G, and Körber KA. inventors; German Patent  DE10239274A1.  2004; Chem. Abstr. 2004, 140, 217823
  • 29 Zuend SJ. Jacobsen EN. J. Am. Chem. Soc.  2007,  129:  15872