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Synthesis 1992; 1992(11): 1080-1082
DOI: 10.1055/s-1992-26307
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
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Publikationsverlauf
Publikationsdatum:
17. September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/199211/lookinside/thumbnails/10.1055-s-1992-26307-1.jpg)
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.