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New synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A key intermediate in the synthesis of epibatidine and analogs

✍ Scribed by Lawrence E. Brieaddy; Feng Liang; Philip Abraham; Jeffrey R. Lee; F. Ivy Carroll

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 110 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01077-6

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✦ Synopsis

A new, high yield, convenient synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1 ]hept-2erie which involved the addition of tributyltin hydride to 7-(tert-butoxycarbonyl)-2-p-toluenesulfonyl-7azabicyclo[2.2.1]-2-ene followed by elimination of the tributyltin and p-tolylsulfonyl groups using tetrabutylammonium fluoride was developed.

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