Title
A Short Synthesis of 1-Azaadamantan-4-one and the syn and anti Isomers of 4-Amino-1-azaadamantane
Document Type
Article
Publication Date
1992
Publication Title
Synthesis
Volume
1992
Issue
11
Pages
1080-1082
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.
Recommended Citation
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
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Copyright Statement
© 1992 Georg Thieme Verlag
Comments
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