Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate

Steven Gareth Williams A D , Mohan Bhadbhade B , Roger Bishop C and Alison Thavary Ung A
+ Author Affiliations
- Author Affiliations

A School of Mathematical and Physical Sciences, University of Technology Sydney, PO Box 123, Broadway, NSW 2007, Australia.

B Mark Wainwright Analytical Centre, University of New South Wales, Sydney, NSW 2052, Australia.

C School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.

D Corresponding author. Email: Steven.Williams@uts.edu.au

Australian Journal of Chemistry - https://doi.org/10.1071/CH17270
Submitted: 16 May 2017  Accepted: 29 June 2017   Published online: 19 July 2017

Abstract

The reaction of (–)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.


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