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

✍ Scribed by Satendra Singh; Garo P. Basmadjian

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
110 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

heptane, an important intermediate for the synthesis of epibatidine and its analogs was efficiently synthesized from N-BOC-exo-2-(methoxycarbonyl)-7azabicyclo[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.

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ChemInform Abstract: A New [4 + 2] Cyclo
ChemInform Abstract: A New [4 + 2] Cycloaddition Strategy for the Synthesis of N-Acyl-7-azabicyclo[2.2.1]heptan-2-ones: A Formal Synthesis of (.+-.)-Epibatidine.
✍ M. L. TRUDELL; N. P. PAVRI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 2 views

A New [4 + 2] Cycloaddition Strategy for the Synthesis of N-Acyl-7-azabicyclo[2.2.1]heptan-2-ones: A Formal Synthesis of (±)-Epibatidine. -The title compound (VIII), an intermediate for the preparation of (±)-epibatidine, is prepared via Diels-Alder reaction of allenes with N-acylated pyrrole (II)