C (8) substituted 1-azabicyclo [3.3. 1] non-3-enes and C (8) substituted 1-azabicyclo [3.3. 1] nonan-4-ones: novel muscarinic receptor antagonists

…, ET Bodor, C Wang, TK Harden, H Kohn

Index: Kim, Myoung Goo; Bodor, Erik T.; Wang, Chen; Harden, T. Kendall; Kohn, Harold Journal of Medicinal Chemistry, 2003 , vol. 46, # 11 p. 2216 - 2226

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Citation Number: 7

Abstract

Expedient syntheses of C (8) substituted 1-azabicyclo [3.3. 1] non-3-enes and C (8) substituted 1-azabicyclo [3.3. 1] nonan-4-ones are reported to begin with 2, 5-disubstituted pyridines. Catalytic reduction of the pyridine to the piperidine followed by treatment with ethyl acrylate and Dieckmann cyclization gave diastereomeric mixtures of C (8) substituted 3- ethoxycarbonyl-4-hydroxy-1-azabicyclo [3.3. 1] non-3-enes, which were separable by ...