PYRROLIDINE DERIVATIVES AND A METHOD OF THEIR SYNTHESIS Russian patent published in 1994 - IPC

FIELD: organic chemistry. SUBSTANCE: product - derivatives of pyrrolidine of the formula (I), where Y - -(CH₂)_n-group, at n = 0; X - H, halogen, lower alkyl, R - phenyl unsubstituted or substituted with halide, lower alkyl, hydroxy- or alkoxy-group, trifluoromethyl; naphthyl; thiophene unsubstituted or substituted with lower alkyl; benzothiophene; pyridyl; imidazole substituted with lower alkyl. At n = 1, X - H or halogen, R - phenyl unsubstituted or substituted with haloid, hydroxy- or alkoxy-group, lower alkyl; thiophene; Y-S(O)_p where p = 0 or 2, -O- or NH, X - H, R-phenyl. Reagent 1: compound of the formula (II) R-Y-CHCOOR₁ where R - as indicated above, R₁ - lower alkyl. Reagent 2: β-nitroarylethane of the formula (III) where R₂ - hydroxy-protective group, X - as indicated above. Synthesized compound of the formula (IV) is reduced to amino-compound which is cyclized, and formed mixture of cis- and trans-form of five-member lactam of the formula (V) is heated in the presence or absence of base in the medium of organic solvent. Synthesized five-member lactam in trans-form is reduced with diborane or complex metal hydride following by removal of protective groups R₂. Synthesized compounds show hypotensive activity. EFFECT: improved method of synthesis. 6 tbl