A Short Synthesis of 1-Azaadamantan-4-one and the 4r and 4s Isomers of 4-Amino-1-azaadamantane
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (11) , 1080-1082
- https://doi.org/10.1055/s-1992-26307
Abstract
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.Keywords
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