NOVEL METHOD FOR PREPARING 4-AMINOMETHYL-3-ALKOXYIMINOPYRROLIDINE METHANESULFONATE (VARIANTS), INTERMEDIATE COMPOUNDS AND METHOD FOR PREPARING QUINOLONE ANTIBIOTICS Russian patent published in 2007 - IPC C07D207/22 C07D471/04 

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel improved methods for synthesis of 4-aminomethyl-3-alkoxyiminopyrrolidine methanesulfonate of the formula (I) that represents a novel intermediate compound used in synthesis of the known quinolone compounds of the formula (VI) possessing antibiotic properties. In compounds of the formula (I) and (VI) R represents (C₁-C₄)-alkyl or (C₁-C₄)-halogenalkyl. Method for synthesis of compound of the formula (I) involves the following steps: (a) interaction of compound of the formula (II) with alkoxyamine or halogenalkoxyamine or their salt in the presence of a base to yield compound of the formula (III); (b) interaction of compound of the formula (III) with methanesulfonic acid to yield compound of the formula (IV); (c) hydrogenation of compound of the formula (IV) with addition of sufficient amounts of methanesulfonic acid and metal-containing hydrogenation catalyst to yield compound of the formula (I). The process can be carried out without isolation of compound of the formula (IV) (step b) adding metal-containing hydrogenation catalyst and the corresponding amount of methanesulfonic acid to compound of the formula (III) directly. Compound of the formula (VI) is prepared from synthesized compound of the formula (I) by its interaction with compound of the formula (V). Also, invention relates to novel compounds of the formula (III) and (IV).

EFFECT: improved methods of synthesis.

27 cl