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Synthesis 1992; 1992(11): 1080-1082
DOI: 10.1055/s-1992-26307
short paper
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A Short Synthesis of 1-Azaadamantan-4-one and the 4r and 4s Isomers of 4-Amino-1-azaadamantane

Daniel P. Becker* , Daniel L. Flynn
  • *Gastrointestinal Diseases Research Department, Searle Research and Development, 4901 Searle Parkway, Skokie, Illinois 60077-1034, USA
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Publication Date:
17 September 2002 (online)

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Reductive homologation of 1,4-cyclohexanedione monoethylene acetal (1) with tosylmethylisocyanide and subsequent reduction with lithium aluminum hydride gave 1,4-dioxaspiro[4.5]decan-8-ylmethylamine (3) which was converted to 1-azatricyclo[3.3.1.13,7] decan-4-one (4) via a known double-Mannich condensation. Reductive amination of this ketone gave the corresponding 1-azatricyclo [3.3.1.13,7]decan-4(s and r)-amines (9 and 10) which were separated on a multigram scale as their corresponding tosylamides 7 and 8, followed by deprotection.