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.

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

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.