A Rapid Access to (±)-Sedamine and Some Original N-Benzyl Unsaturated Analogues

Abstract

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity.

hydrides - diastereoselectivity - piperidines - pyridinium - reduction

References

<A NAME="RZ07110SS-1">1</A> Marion L. Can. J. Res.  1945,  23B:  165 

<A NAME="RZ07110SS-2">2</A> Gupta RN. Spenser ID. Can. J. Chem.  1967,  45:  1275 

<A NAME="RZ07110SS-3">3</A> Wieland H. Koschara ED. Renz J. Schwarze W. Linde W. Justus Liebigs Ann. Chem.  1939,  540:  103 

<A NAME="RZ07110SS-4">4</A> Damaj MJ. Patrick GS. Creasy KR. Martin BR.
J. Pharmacol. Exp. Ther.  1997,  282:  410 

<A NAME="RZ07110SS-5">5</A> Flammia D. Dukat M. Damay MI. Martin B. Glennon RA. J. Med. Chem.  1999,  42:  3726 

<A NAME="RZ07110SS-6">6</A> Terry AV. Williamson R. Gattu M. Beach JW. McCurdy CR. Sparks JA. Pauly JR. Neuropharmacology  1998,  37:  93 

<A NAME="RZ07110SS-7">7</A> Watson PS. Jiang B. Scott B. Org. Lett.  2000,  2:  3679 

<A NAME="RZ07110SS-8A">8a</A> Bates RW. Sa-Ei K. Tetrahedron  2002,  58:  5957 

<A NAME="RZ07110SS-8B">8b</A> Felpin F.-X. Lebreton J. Tetrahedron  2004,  60:  10127 

<A NAME="RZ07110SS-9A">9a</A> Felpin F.-X. Lebreton J. J. Org. Chem.  2002,  67:  9192 

<A NAME="RZ07110SS-9B">9b</A> Bates RW. Nemeth JA. Snell RH. Synthesis  2008,  1033 ; and literature cited therein

<A NAME="RZ07110SS-10">10</A> Felpin F.-X. Lebreton J. Tetrahedron Lett.  2002,  43:  225 

<A NAME="RZ07110SS-11A">11a</A> Beyerman HC. Eveleens W. Muller YMF. Recl. Trav. Chim. Pays-Bas  1956,  75:  63 

<A NAME="RZ07110SS-11B">11b</A> Beyerman HC. Eenshuistra J. Eveleens W. Zweistra A. Recl. Trav. Chim. Pays-Bas  1959,  78:  43 

Recent reviews:

<A NAME="RZ07110SS-12A">12a</A> Felpin F.-X. Lebreton J. Eur. J. Org. Chem.  2003,  67:  3693 

<A NAME="RZ07110SS-12B">12b</A> Weintraub PM. Sabol JS. Kane JM. Borcherding DR. Tetrahedron  2003,  59:  2953 

<A NAME="RZ07110SS-12C">12c</A> Buffat MGP. Tetrahedron  2004,  60:  1701 

<A NAME="RZ07110SS-12D">12d</A> Escolano C. Amat M. Bosch J. Chem. Eur. J.  2006,  12:  8198 

<A NAME="RZ07110SS-13">13</A> For a review on this topic, see: Felpin F.-X. Lebreton J. Curr. Org. Synth.  2004,  1:  83 

<A NAME="RZ07110SS-14">14</A>

The diastereoisomeric ratio was determined by GC analysis [Optima 3 column (Macherey-Nagel), 80 ˚C, 1 min, 12 ˚C/min, 250 ˚C, 1 min, 12 ˚C/min, 300 ˚C]: t _R = 19.8 min [(±)-10a; 16%); 21.08 min ((±)-9a; 21%); 20.88 and 23.40 min [(±)-7a and (±)-8a, 42% and 21%, respectively].

<A NAME="RZ07110SS-15A">15a</A> For compounds 7a and 8a, see: Compère D. Marazano C. Das BC. J. Org. Chem.  1999,  64:  4528 

<A NAME="RZ07110SS-15B">15b</A>

For compound 10a, see ref. 9b.

<A NAME="RZ07110SS-16A">16a</A> Dondoni A. Fantin G. Fogagnolo M. Tetrahedron Lett.  1989,  30:  6063 

<A NAME="RZ07110SS-16B">16b</A> Evans DA. Chapman KT. Carreira EM. J. Am. Chem. Soc.  1988,  110:  3560 

<A NAME="RZ07110SS-17">17</A> Jedrzejewska B. Kabatc J. Pietrzak M. Paczkowski J. Dyes Pigm.  2003,  58:  47 

<A NAME="RZ07110SS-18A">18a</A> For a very interesting overview of asymmetric hydrogenation of aromatic compounds including pyridines, see: Glorius F. Org. Biomol. Chem.  2005,  3:  4171 

<A NAME="RZ07110SS-18B">18b</A> For more specific preparation of tetrahydropyridine derivatives in this context, see: Legault C. Charette AB. J. Am. Chem. Soc.  2003,  125:  6360 

<A NAME="RZ07110SS-19">19</A> Katoh T. Kirihara M. Nagata Y. Kobayashi Y. Arai K. Minami J. Terashima S. Tetrahedron Lett.  1993,  34:  5747 

<A NAME="RZ07110SS-20">20</A> Tirel P.-J. Vaultier M. Carrié R. Tetrahedron Lett.  1989,  30:  1947