ENANTIOSELECTIVE METHOD FOR SYNTHESIS OF QUINOLINE DERIVATIVES Russian patent published in 2010 - IPC C07D215/26 

FIELD: chemistry.

SUBSTANCE: present invention relates to a method for synthesis of 8-phenylmethoxy-5-((R)-2-halogen-1-hydroxyethyl)-(1H)-quinolin-2-ones or their acceptable solvates, involving reaction of 5-(α-halogenacetyl)-8-phenylmethoxy-(1H)-quinolin-2-one with a reducing agent in the presence of a chiral agent and a base to form 8-phenylmethoxy-5-((R)-2-halogen-1-hydroxyethyl)-(1H)-quinolin-2-one, where the said chiral agent is characterised by formula

or ,

where M represents Ru, Rh, Ir, Fe, Co or Ni, L represents C₆-C₂₄aryl or C₆-C₂₄aryl(C₁-C₁₀)aliphatic residue, in any case optionally bonded to a polymer, X represents hydrogen or halogen, R¹ represents C₁-C₁₀aliphatic, C₃-C₁₀cycloaliphatic, C₃-C₁₀cycloaliphatic(C₁-C₁₀)aliphatic, C₆-C₂₄aryl or C₆-C₂₄aryl(C₁-C₁₀)aliphatic residue to a 4-12-member heterocyclic group which is optionally bonded to a polymer in each case, and R² and R³ represent phenyl, or R² and R³ together with the carbon atom to which they are bonded form cyclohexane or cycloheptane. The invention also relates to a method for synthesis of salts of 5-[(R)-2-(5,6-diethylindan-2-ylamino)-l-hydroxyethyl]-8-hydroxy-(1H)-quinolin-2-one, one of the steps of is synthesis of 8-phenylmethoxy-5-((R)-2-halogen-1-hydroxyethyl)-(1H)-quinolin-2-ones.

EFFECT: design of a new cheap and highly efficient enantioselective method for synthesis of quinoline derivatives.

10 cl, 1 tbl, 11 ex