76596-55-9Relevant academic research and scientific papers
Chemoenzymatic Synthesis of Chiral Isoxazole Derivatives
Amici, Marco De,Micheli, Carlo De,Carrea, Giacomo,Spezia, Sandro
, p. 2646 - 2650 (2007/10/02)
The synthesis of the two enantiomers of 1-(3-bromo-5-isoxazolyl)-2-(tert-butylamino)ethanol (1), a potent and selective β2-adrenergic stimulant, has been efficiently accomplished by enzyme-catalyzed transformations.The absolute configurations are attributed to (+)- and (-)-1 by correlation with (S)-3-butyn-2-ol.The S enantiomer was prepared in >98percent enantiomeric excess by reducing α-bromo ketone 4 in the presence of alcohol dehydrogenase from Thermoanaerobium brockii and the R enantiomer was obtained in 97percent ee through a kinetic resolution of the racemic bromohydrin(+/-)-5, in organic solvents, catalyzed by lipase P from Pseudomonas fluorescens.The experimental conditions for the lipase-catalyzed asymmetric transesterifications were optimized in order to improve reaction rates and the enantiomeric excess of the products.
1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol
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, (2008/06/13)
A new isoxazole derivative and the preparation thereof are disclosed. 1-(3-Bromo-isoxazol-5-yl)-2-ter.butylaminoethanol endowed with therapeutic activity, in particular bronchodilating action is disclosed, as well as a method for preparing same from 3-bromo-5-isoxazolecarboxylic acid. New intermediate compounds as well as pharmaceutical compositions containing the novel isoxazole derivative are also disclosed.
