From pregabalin to rac-3-cyano-5-methylhexanoic acid : an easy conversion which valorizes waste pregabalin enantiomer
Articolo
Data di Pubblicazione:
2012
Citazione:
From pregabalin to rac-3-cyano-5-methylhexanoic acid : an easy conversion which valorizes waste pregabalin enantiomer / M. Zagami, M. Binda, O. Piccolo, V. Straniero, E. Valoti, M. Pallavicini. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 53:45(2012 Nov 07), pp. 6075-6077. [10.1016/j.tetlet.2012.08.128]
Abstract:
(S)-(+)-3-Aminomethyl-5-methylhexanoic acid (pregabalin) was converted in one-pot to (S)-(-)-3-cyano-5-methylhexanoic acid (pregabalin nitrile) by N-dichlorination and double dehydrochlorination. The (S) β-cyanoacid was racemized under mild conditions by treatment with a base. This very simple and efficient procedure, applied to (R)-(-)-3-aminomethyl-5-methylhexanoic acid, would enable the recycling of the undesired enantiomer of pregabalin, an anticonvulsant drug manufactured by the synthesis of rac-3-aminomethyl-5- methylhexanoic acid and subsequent classical resolution.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Dichloroamine; Pregabalin; Pregabalin nitrile; Racemization; Trichloroisocyanuric acid
Elenco autori:
M. Zagami, M. Binda, O. Piccolo, V. Straniero, E. Valoti, M. Pallavicini
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