A Short Synthesis of 1-Azaadamantan-4-one and the syn and anti Isomers of 4-Amino-1-azaadamantane
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[18.104.22.168,7] decan-4-one (4) via a known double-Mannich condensation. Reductive amination of this ketone gave the corresponding 1-azatricyclo [22.214.171.124,7]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.
Becker, Daniel P. and Flynn, Daniel L.. A Short Synthesis of 1-Azaadamantan-4-one and the syn and anti Isomers of 4-Amino-1-azaadamantane. Synthesis, 1992, 11: 1080-1082, 1992. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1055/s-1992-26307
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© 1992 Georg Thieme Verlag