(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.
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]
From pregabalin to rac-3-cyano-5-methylhexanoic acid : an easy conversion which valorizes waste pregabalin enantiomer
M. BindaSecondo
;V. Straniero;E. ValotiPenultimo
;M. Pallavicini
Ultimo
2012
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.File | Dimensione | Formato | |
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Tetrahedron Letters 53 (2012) 6075-772.pdf
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