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Synthesis 2000; 2000(4): 521-524
DOI: 10.1055/s-2000-6363
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Lipase-Mediated Synthesis of Enantiopure N-Carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydro- and N-Carbobenzoxy-3-hydroxy-1,2,3,6-tetrahydropyridines from 3-Hydroxypyridine

Hideki Sakagami* , Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81 (22) 2 17 68 45; E-mail: konol@mail.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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Two isomeric chiral hydroxytetrahydropyridines, having high potential utility for the construction of a variety of chiral amine derivatives, have been prepared in both enantiomeric forms by employing lipase-mediated resolution starting from 3-hydroxypyridine. Thus, on exposure to sodium borohydride in the presence of carbobenzoxy chloride, 3-hydroxypyridine has been found to furnish racemic N-carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydropyridine, which is resolved under trans-esterification conditions in the presence of lipase PS to give both enantiomeric products in enantiopure forms. Isomerization of the chiral 1,2,3,4-tetrahydro-product into the chiral 1,2,3,6-tetrahydro-derivative has been accomplished without loss of the original chiral integrity. The racemic 1,2,3,6-tetrahydro-derivative has also been resolved under the same lipase-mediated trans-esterification conditions.

lipase-mediated kinetic resolution - trans-esterification - chiral building block - tetrahydropyridinol - regioselective reduction