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ChemInform Abstract: New Synthesis of 7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A Key Intermediate in the Synthesis of Epibatidine and Analogues.

✍ Scribed by L. E. BRIEADDY; F. LIANG; P. ABRAHAM; J. R. LEE; F. I. CARROLL

Publisher: John Wiley and Sons
Year: 2010
Weight: 31 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199842214

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✦ Synopsis

New Synthesis of 7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A Key Intermediate in the Synthesis of Epibatidine and Analogues.

-In continuation of efforts on efficient synthetic routes to the alkaloid epibatidine (V), an improved procedure for the synthesis of the N-Boc protected azabicycloheptene (IV) is reported. Thus, radical addition of tributyltin hydride to the precursor (I) and fluoride-induced elimination provides an efficient access to (IV), allowing the synthesis of gram amounts of epibatidine.

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