Synthesis and Molecular Structure of Chiral (2S, 5S)-tert-Butyl 3-Oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate. (5th November 2014)

• Record Type: Journal Article
• Authors: Moriguchi, Tetsuji; Krishnamurthy, Suvratha; Arai, Toru; Tsuge, Akihiko
• Other Names: Mino Takashi Academic Editor.
• Is Part Of: Journal of crystallography. Volume 2014(2014)
• Publication Date: 2014-11-05
• Subjects: Crystallography -- Periodicals; Crystallography; Periodicals; 548
• DOI: 10.1155/2014/150796
• Languages: English
• ISSNs: 2356-7317

Abstract

Abstract : The title compound (2 S, 5 S )- 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 1 H 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 P21 21 21 (No. 19, noncentrosymmetric, chiral) witha = 9.6402 ( 10 ) Å, b = 9.7026 ( 10 ) Å, c = 12.2155 ( 12 ) Å, D calc = 1.319 4 g/cm 3, 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.