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DOI: 10.1039/A904394B (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 3527-3530

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

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Aigars Jirgensons, Valerjans Kauss, Anatolij F. Mishnev and Ivars Kalvinsh

Abstract

1,3,5,7α- and 1,3,5,7β-Tetramethylbicyclo[3.3.1]nonan-3-ols 3a and 3b were prepared from the corresponding ketones 2a and 2b. 7α-Methyl isomer 3a gave selectively endo-3α-N-formylaminobicyclononane 10 in the Ritter reaction with trimethylsilyl cyanide. 7β-Methyl epimer 3b suffered water elimination resulting in bicyclo[3.3.1]non-2-ene 12 under the same reaction conditions. The endo-amide structure was confirmed by X-ray analysis..

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