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

doi:10.1155/2014/645079

Paper

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

Published Aug 17, 2014 · T. Moriguchi, Suvratha Krishnamurthy, T. Arai

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Abstract

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 A, A, A, 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.

Study Snapshot

Tert-butyl 3-oxo-2-oxa-5-azabicyclo(2.2.2)octane-5-carboxylate is a novel synthetic compound with a unique bicyclo[2.2.2]octane structure and two diastereomers present in a

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

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

The chiral compound (2S, 5S)-tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized without chiral catalyst or enzyme and has a bicyclo[2.2.2]