Data di Pubblicazione:
2013
Citazione:
Diastereomeric 2-aminomethyl-1,4-benzodioxane mandelates : phase diagrams and resolution / C. Bolchi, M. Pallavicini, L. Fumagalli, P. Ruggeri, E. Valoti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 24:13-14(2013), pp. 796-800. [10.1016/j.tetasy.2013.05.010]
Abstract:
The diastereomeric salts of (R)- and (S)-2-aminomethyl-1,4-benzodioxane with unichiral mandelic acid form a simple eutectic, whose binary phase melting point diagram shows the unique eutectic at 0.35 M ratio of the less soluble diastereomer. Such an eutectic composition, near to 0.5, is consistent with the modest efficiency previously reported for their separation via crystallization from ethanol/ethyl acetate. However, the ternary solubility phase diagram, obtained from solubility measurements in methanol, shifts the eutectic to a lower molar ratio (0.10) of the less soluble diastereomer, thus indicating an optimal resolvability of the diastereomeric mandelates. This was confirmed by the highly efficient resolution of racemic 2-aminomethyl-1,4-benzodioxane with (R)-mandelic acid via a single crystallization from methanol. The ready availability of both the racemic substrate and the resolving acid makes this simple and efficient resolution procedure very attractive to obtain the enantiomers of 2-aminomethyl-1,4-benzodioxane, which are important synthetic intermediates.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
C. Bolchi, M. Pallavicini, L. Fumagalli, P. Ruggeri, E. Valoti
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