N-Chlorination by sodium dichloroisocyanurate and dehydrochlorination by TEA, followed by hydrogenation, allowed (1R,6S)-8-benzyl-7,9-dioxo-2,8- diazabicyclo[4.3.0]nonane to be quantitatively racemised and the resulting trans-free cis racemate to be recycled into the resolution process to yield (1S,6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane, a key intermediate of moxifloxacin.
Highly efficient racemisation of a key intermediate of the antibiotic moxifloxacin / M. Pallavicini, C. Bolchi, L. Fumagalli, O. Piccolo, E. Valoti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 22:4(2011 Feb 24), pp. 379-380. [10.1016/j.tetasy.2011.02.007]
Highly efficient racemisation of a key intermediate of the antibiotic moxifloxacin
M. Pallavicini;C. Bolchi;L. Fumagalli;E. Valoti
2011
Abstract
N-Chlorination by sodium dichloroisocyanurate and dehydrochlorination by TEA, followed by hydrogenation, allowed (1R,6S)-8-benzyl-7,9-dioxo-2,8- diazabicyclo[4.3.0]nonane to be quantitatively racemised and the resulting trans-free cis racemate to be recycled into the resolution process to yield (1S,6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane, a key intermediate of moxifloxacin.
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