470669-26-2Relevant articles and documents
A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidines
Sato, Tatsunori,Yamazaki, Taro,Nakanishi, Yumi,Uenishi, Jun-ichi,Ikeda, Masazumi
, p. 1438 - 1443 (2007/10/03)
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 synthesis of (±)-euphococcinine.