One pot synthesis of 2-oxazolidinone derivatives

Details One pot synthesis of 2-oxazolidinone derivatives One pot synthesis of 2-oxazolidinone derivatives

C - Chemistry, Metallurgy

07

D

C07D 413/06 (2006.01)

Patent

CA 2572508

The present invention provides an improved process for preparing (S)-4-([3-[2- (dimethylamino)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone which comprises: a) forming a carbamate of formula (III), from methyl 4nitro- (L)-phenylalaninate hydrochloride; b) reducing the compound of formula (III) to give the compound of formula (IV); c) reducing the methyl ester grouping in the compound of formula (IV) to give the compound of formula (V); d) ring closure of the compound of formula (V) to give the compound of formula (VI); e) diazonium salt formation from the compound of formula (VI) followed by reduction to give the compound of formula (VII); f) Fischer reaction of the compound of formula (VII) to give (S)-4-{[3-[2- (dimethylamino)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone.

La présente invention porte sur un procédé amélioré de préparation de (S)-4-(¬3-¬2- (diméthylamino)éthyle|-1H-indol-5-yl|méthyle}-2-oxazolidinone, qui comprend les étapes suivantes : a) former un carbamate de la formule (III), à partir du méthyle 4nitro- (L)-phenylalaninate chlorhydrate; b) réduire le composé de la formule (III) pour obtenir le composé de la formule(IV); c) réduire le groupe d'ester méthylique dans le composé de la formule (IV) pour obtenir le composé de la formule (V); d) cyclisation du composé de la formule (V) pour obtenir le composé de la formule (VI); e) formation de sel de diazonium à partir du composé de la formule (VI), suivie d'une réduction pour obtenir le composé de la formule (VII); f) réaction Fischer du composé de la formule (VII) pour obtenir (S)-4-{¬3-¬2- (diméthylamino)éthyle|-1H-indol-5-yl|méthyle}-2-oxazolidinone.

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