METHOD FOR STEREOCHEMICALLY CONTROLLING PREPARING ISOMERICALLY PURE HIGH-SUBSTITUTED AZACYCLIC COMPOUNDS Russian patent published in 2004 - IPC

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to stereochemically controlling method for preparing azacyclic compounds of the formula (Ia') wherein R¹R²CH-group at 5-position of cyclic fragment and hydroxy- group at 3-position of cyclic member are in trans-position relative to each other and wherein substituent R⁴ at 4-position and hydroxy-group at 3-position of cyclic fragment are in cis-position relative to each other and wherein n = 0 or 1; R¹-R³ mean hydrogen atom; R⁴- means hydrogen atom or lower alkyl; or R³ and R⁴ mean in common C₂-C₆-alkylene chain; R⁵-R⁷ mean hydrogen atom; R⁸- means hydrogen atom, lower alkyl, (lower alkoxy)-lower alkyl, phenyl or phenyl-lower alkyl; R⁶ and R⁷ can form also in common a linkage; R⁵ and R⁸ in common with carbon atoms with which they are bound can form aromatic C₆-ring system; R⁹- means hydrogen atom or protective amino-group; or R⁸ and R⁹ can form in common C₃-C₄-alkylene chain, or their salts. Method for preparing involves interaction of compound of the formula (II) with a base, organometallic compound and stereoisomer of compound of the formula (VIII) to form stereoisomer of compound of the formula (IX) that by treatment with suitable reagent is converted to compound of the formula (Xa) and this compound is treated with samarium (II) iodide followed by if necessary splitting off protective groups. Method provides preparing high-substituted azacyclic compounds in isomerically pure form and with high yield. Invention describes intermediate compounds of the formula (Xa) also. EFFECT: improved preparing method. 10 cl, 1 tbl, 5 ex