COMPOUNDS AND METHODS FOR PREPARING METHANESULFONAMIDES

A process for preparing (S)-(-)-N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl ]methanesulfonamide hemifumarate salt, which comprises reacting N-[4[(2S)-tetrahydro-5-hydroxy-2-furanyl]phenyl]methanesulfonamide (IIa) with fluoroamine (III) in the presence of triacetoxyborohydride and ethyl acetate to provide [4-[-4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl]methanes ulfonamide (I) and then converting I into the hemifumarate salt Ia. A process for preparing IIa is also claimed as well as intermediates IIa-IId. A process for preparing (S)-(-)-N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl]methanesulfonamide hemifumarate salt, which comprises reacting N-[4[(2S)-tetrahydro-5-hydroxy-2-furanyl]phenyl]methanesulfonamide (IIa) with fluoroamine (III) in the presence of triacetoxyborohydride and ethyl acetate to provide [4-[-4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl]methanesulfonamide (I) and then converting I into the hemifumarate salt Ia. A process for preparing IIa is also claimed as well as intermediates IIa-IId. La présente invention concerne un procédé permettant d'élaborer le sel (S)-(-)-N-[4-[4-[éthyle(6-fluoro-6-méthyleheptyl)amino]-1-hydroxy]phényle]méthanesulfonamide-hémifumarate. Ce procédé implique de faire réagir du N-[4[(2S)-tétrahydro-5-hydroxy-2-furanyle]phényle]méthanesulfonamide (IIa) avec du fluoroamine (III) en présence de triacétoxyborohydrure et de l'acétate d'éthyle de façon à donner du [4-[-4-[éthyle(6-fluoro-6-méthyleheptyle)amino]-1-hydroxy]phényle]méthanesulfonamide (I), puis de convertir ce dernier (I) pour donner le sel hémifumarate (Ia). L'invention concerne également un procédé permettant l'élaboration du méthanesulfonamide (IIa) ainsi que des intermédiaires (IIa à IId).