Table of Contents
Journal of Crystallography
Volume 2014, Article ID 150796, 6 pages
http://dx.doi.org/10.1155/2014/150796
Research Article

Synthesis and Molecular Structure of Chiral (2S, 5S)-tert-Butyl 3-Oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate

Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan

Received 15 July 2014; Accepted 1 October 2014; Published 5 November 2014

Academic Editor: Takashi Mino

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.

Abstract

The title compound (2S, 5S)-tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a chiral cyclic amino acid ester from the corresponding cis- and trans-5-hydroxypipecolic acid ethyl esters via an intramolecular lactonization reaction without using chiral catalyst or enzyme and without separation by chiral column chromatography. The chiral compound was characterized using 1H NMR spectroscopy and high-resolution mass spectrometry. Its exact structure was then determined via single crystal X-ray diffraction analysis of a single crystal obtained after recrystallization of the compound from ethyl acetate/diethyl ether. The crystal was found to be of the orthorhombic space group P212121 (No. 19, noncentrosymmetric, chiral) with  Å,  Å,  Å, 4 g/cm3, and a Flack parameter of 0.0(5) at 90 K. The compound has a bicyclo[2.2.2]octane structure comprised of lactone and piperidine groups.