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) C07C 271/16 (2006.01) C07C 271/20 (2006.01) C07C 271/22 (2006.01) C07D 263/20 (2006.01)

Patent

CA 2227039

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 4-nitro- (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.

L'invention concerne un procédé amélioré de préparation de (S)-4-{[3-[2-(diméthylamino)éthyl]-1H-indol-5-yl]méthyl}-2-oxazolidinone, ce qui consiste à: a) former un carbamate de formule (III) à partir d'hydrochlorure de méthyle 4-nitro-(L)-phénylalaninate; b) réduire le composé de formule (III) afin d'obtenir le composé de formule (IV); c) réduire le groupe d'ester de méthyle dans le composé de formule (IV) afin d'obtenir le composé de formule (V); d) fermer le noyau du composé de formule (V) afin d'obtenir le composé de formule (VI); e) former un sel de diazonium à partir du composé de formule (VI) puis le réduire afin d'obtenir le composé de formule (VII); f) procéder à une réaction de Fischer du composé de formule (VII) afin d'obtenir (S)-4-{[3-[2-(diméthylamino)éthyl]-1H-indol-5-yl]méthyl}-2-oxazolidinone.

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