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…

文献索引：Zagami, Michael; Binda, Matteo; Straniero, Valentina; Valoti, Ermanno; Pallavicini, Marco; Piccolo, Oreste Tetrahedron Letters, 2012 , vol. 53, # 45 p. 6075 - 6077,3

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被引用次数: 5

摘要

(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 ...