Efficient synthesis of (±)-N-BOC- exo-2-(methoxycarbonyl)-7-Azabicyclo[2.2.1]heptane, a versatile intermediate for the synthesis of epibatidine and epiboxidine

N-BOC- exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]heptane, an important intermediate for the synthesis of epibatidine and its analogs was efficiently synthesized from N-BOC- exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]hepta-2,5-diene ( 5) via hydrogenation followed by reductive dehalogenation or via...

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Bibliographic Details
Published in:Tetrahedron letters 1997-09, Vol.38 (39), p.6829-6830
Main Authors: Singh, Satendra, Basmadjian, Garo P.
Format: Article
Language:English
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Summary:N-BOC- exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]heptane, an important intermediate for the synthesis of epibatidine and its analogs was efficiently synthesized from N-BOC- exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]hepta-2,5-diene ( 5) via hydrogenation followed by reductive dehalogenation or via hydrodehalogenation followed by epimerization. The diene 5 was obtained by Diels-Alder reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01606-7