A Short Synthesis of 1-Azaadamantan-4-one and the syn and anti Isomers of 4-Amino-1-azaadamantane
Author Posting. © Georg Thieme Verlag, 1992. This is the author's version of the work. It is posted here by permission of Georg Thieme Verlag for personal use, not for redistribution. The definitive version was published in Synthesis 1992; 1992(11): 1080-1082. http://dx.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.
