Table of Contents
Journal of Crystallography
Volume 2014, Article ID 645079, 6 pages
Research Article

Synthesis and Molecular Structure of tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate

1Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan
2Evaluation Center of Materials Properties and Function, Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan
3Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, 2-4 Hibikino, Wakamatsu-ku, Kitakyushu 808-0196, Japan

Received 2 April 2014; Accepted 19 June 2014; Published 17 August 2014

Academic Editor: Mehmet Akkurt

Copyright © 2014 Tetsuji Moriguchi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


The compound tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a cyclic amino acid ester from the corresponding ethyl 2-amino-4-(2-oxiranyl)butanoate HCl salt via an intramolecular lactonization reaction and was characterized by using 1H NMR spectroscopy and high-resolution mass spectrometry. The product was then recrystallized from dichloromethane/diethyl ether and its structure was determined via single crystal X-ray diffraction analysis. The crystal was found to be of the monoclinic space group P21/c (no. 14) with  Å,  Å,  Å, β = 114.186(13)°, and = 1.350 g/cm3 at 123 K. The compound has bicyclo[2.2.2]octane structure including a lactone moiety and a piperidine ring, and the two diastereomers of the molecules are present in a 1 : 1 ratio in the crystal.