Unlike the diastereomeric 1-phenylethylammonium salts, the diastereomeric N-1-phenylethylamides of (S)- and (R)-1,4-benzodioxane-2-carboxylic acid show significant differences in fusibility and solubility so as to be efficiently resolved by precipitation of the less soluble diastereomer (>98% de), while chromatographic purification of the unprecipitated fraction affords the more soluble one (>99% de). Overall, 95% of the former and 80% of the latter are recovered. The hydrolysis of the two resolved amides provides the two acid enantiomers and the resolving amine in quantitative yield and with unchanged stereoisomeric purity.

Crystallization-based resolution of 1,4-benzodioxane-2-carboxylic acid enantiomers via diastereomeric 1-phenylethylamides / L. Fumagalli, C. Bolchi, F. Bavo, M. Pallavicini. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 57:18(2016), pp. 2009-2011. [10.1016/j.tetlet.2016.03.100]

Crystallization-based resolution of 1,4-benzodioxane-2-carboxylic acid enantiomers via diastereomeric 1-phenylethylamides

L. Fumagalli
Primo
;
C. Bolchi
Secondo
;
F. Bavo
Penultimo
;
M. Pallavicini
2016

Abstract

Unlike the diastereomeric 1-phenylethylammonium salts, the diastereomeric N-1-phenylethylamides of (S)- and (R)-1,4-benzodioxane-2-carboxylic acid show significant differences in fusibility and solubility so as to be efficiently resolved by precipitation of the less soluble diastereomer (>98% de), while chromatographic purification of the unprecipitated fraction affords the more soluble one (>99% de). Overall, 95% of the former and 80% of the latter are recovered. The hydrolysis of the two resolved amides provides the two acid enantiomers and the resolving amine in quantitative yield and with unchanged stereoisomeric purity.
1-Phenylethylamine; 1,4-Benzodioxane-2-carboxylic acid; Covalent diastereomers; Resolution
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
2016
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/417117
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