The synthesis of 3-amino-3-methylbicyclo[3.3.1]nonanes: Endo-selectivity in the Ritter reaction of 1,3,5,7 alpha-tetramethylbicyclo[3.3.1]nonan-3-ol

Authors
Jirgensons, A Kauss, V Mishnev, AF Kalvinsh, I
Citation
A. Jirgensons et al., The synthesis of 3-amino-3-methylbicyclo[3.3.1]nonanes: Endo-selectivity in the Ritter reaction of 1,3,5,7 alpha-tetramethylbicyclo[3.3.1]nonan-3-ol, J CHEM S P1, (23), 1999, pp. 3527-3530
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
23
Year of publication
1999
Pages
3527 - 3530
Database
ISI
SICI code
0300-922X(1999):23<3527:TSO3EI>2.0.ZU;2-3
Abstract
1,3,5,7 alpha- and 1,3,5,7 beta-Tetramethylbicyclo[3.3.1]nonan-3-ols 3a and 3b were prepared from the corresponding ketones 2a and 2b. 7 alpha-Methyl isomer 3a gave selectively endo 3 alpha-N-formylaminobicyclononane 10 in th e Ritter reaction with trimethylsilyl cyanide. 7 beta-Methyl epimer 3b suff ered water elimination resulting in bicyclo[3.3.1]non-2-ene 12 under the sa me reaction conditions. The endo-amide structure was confirmed by X-ray ana lysis..