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
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Authors
Dates
2004-03-10—Published
1999-05-10—Filed