Patent ID: 6084103
Filing Date: 2000-07-04
Classification: A61P,C07C,C07D

Abstract:
A process for the preparation of a (S)-4-{[3-[2(dimethylamino)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone represented by formula (I) ##STR22## which process comprises the steps of a) forming a carbamate from methyl 4-nitro-(L)-phenylalaninate hydrochloride, represented by formula (II) ##STR23## by adding sodium carbonate or sodium hydrogen carbonate and n-butyl chloroformate and reacting to give methyl(S)-N-butoxycarbonyl-4-nitrophenylalaninate, represented by formula (III) ##STR24## b) reducing the compound of formula (III) to give methyl (S)-N-butoxycarbonyl-4-amino phenylalaninate, represented by formula (IV) ##STR25## c) reducing the methyl ester grouping --CO.sub.2 CH.sub.3 in the compound of formula (IV) to give (S)-N-butoxycarbonyl-4-aminophenylalaninol, represented by formula (V) ##STR26## d) a ring closure of the compound of formula (V) without the need for phosgene to give (S)-4-(4-aminobenzyl)-2-oxazolidinone, represented by formula (VI) ##STR27## e) preparation of the diazonium salt of the compound of formula (VI) followed by reduction without the need for tin chloride to give the hydrazine (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone hydrochloride, represented by formula (VII) ##STR28## f) Fischer reaction of the compound of formula (VII) to give the compound of formula (I).