Process for preparation of r-1-(aryloxy)propan-2-ol

Details Process for preparation of r-1-(aryloxy)propan-2-ol Process for preparation of r-1-(aryloxy)propan-2-ol

C - Chemistry, Metallurgy

07

C

C07C 43/205 (2006.01) C07B 53/00 (2006.01) C07C 205/37 (2006.01)

Patent

CA 2406215

A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2- ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1- (2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6- nitrophenyl trimethysilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6- nitrophenoxy)-propan-2-ol in high purity and yield.

L'invention concerne un procédé de préparation du (R)-1-(2,3-difluoro-6-nitrophénoxy)-propan-2-ol, lequel constitue un intermédiaire utile dans la synthèse de l'antibiotique très utilisé, la lévofloxacine. L'invention concerne également un procédé de préparation du (R)-1-(2,3-difluoro-6-nitrophénoxy)-2-triméthylsiloxypropane, consistant à ouvrir le noyau d'oxyde de (R)-propylène à l'aide de 2,3-difluoro-6-nitrophényl-triméthysilyl-éther, en présence d'un catalyseur Co(salen) actif sur le plan optique. Le groupe triméthylsilyle du réactif est transféré dans l'aryloxy alcool produit, lequel sert à protéger le second alcool sur place. Lors de l'isolation, on enlève le groupe triméthylsilyle et on purifie le mélange régio-isomère résultant afin de produire le (R)-1-(2,3-difluoro-6-nitrophénoxy)-propan-2-ol recherché, très pur, et avec un rendement élevé.

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