METHOD OF SYNTHESIS OF DERIVATIVES OF (S)-3-AMINO-1-BENZYLPYRROLIDINE, DERIVATIVES OF (S)-AZIRIDINE AS INTERMEDIATE COMPOUNDS FOR THEIR SYNTHESIS AND 1-BENZYL-3-(S)-, 2-(S)-[(TERT-BUTOXYCARBONYLAMINO)PROPIONYLAMINO]-PYRROLIDINE AS AN INTERMEDIATE COMPOUND FOR QUINOLONE-BASE ANTIBACTERIAL AGENTS Russian patent published in 1998 - IPC

FIELD: organic chemistry. SUBSTANCE: invention relates to method of synthesis of derivatives of (S)-3-amino-1-substituted pyrrolidine involving protection of L-aspartic acid amino-group, treatment of the N-protected L-aspartic acid with using primary amine to obtain derivatives of (S)-3-amino-1-substituted pyrrolidine, removal of protective group and isolation of the end product. L-aspartic acid amino-group is protected by interaction of with alkylsulfonyl- or arylsulfonyl halide and treatment of N-protected L-aspartic acid is carried out by reduction of the latter or its lower dialkyl ester with reducing hydride. The obtained N-protected 1,4-butanediol is interacted with about two equivalents of thionyl chloride or alkylsulfonylhydroxy- or arylsulfonylhydroxy halide in the presence of about three equivalents of a base. The obtained compound of the formula: where Z means alkylsulfonyl or arylsulfonyl and L - halide, alkylsulfonylhydroxy- or arylsulfonylhydroxy is subjected for interaction with primary amine of the formula R-NH₂ where R means unsubstituted benzyl or benzyl substituted with lower alkyl or lower alkoxy, or benzhydryl in the presence of tertiary amine to obtain 1-R-3-(amino-protected)-pyrrolidine where R has a value as indicated above. Protective group is removed by hydrolysis. Invention relates to also derivatives of (S)-aziridine of the formula indicated above where Z means halide or alkylsulfonyl that are intermediate compounds for synthesis of derivatives of (S)-3-amino-1-substituted pyrrolidine. Invention relates to also 1-benzyl-3-(S)-[(tert.-butoxycarbonylamino)propionylamino] -pyrrolidine as an intermediate compound for synthesis of antibacterial agents based on quinolone derivatives. EFFECT: improved method of synthesis. 5 cl