A new entry to 9-azabicyclo [3.3. 1] nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl) piperidines

T Sato, T Yamazaki, Y Nakanishi, J Uenishi…

Index: Sato, Tatsunori; Yamazaki, Taro; Nakanishi, Yumi; Uenishi, Jun-ichi; Ikeda, Masazumi Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 12 p. 1438 - 1443

Full Text: HTML

Citation Number: 0

Abstract

The 2-[4-(trimethylsilyl) but-3-ynyl] piperidines 16a–c, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in refluxing toluene, gave the 9-azabicyclo [3.3. 1] nonanes 17a–c in high yields, respectively. Compound 17c was subjected to desilylation, ozonolysis, and subsequent 1, 2-transposition of the resulting carbonyl group to give 9- benzoyl-1-methyl-9-azabicyclo [3.3. 1] nonan-3-one, a potential precursor for the ...