945920-22-9Relevant academic research and scientific papers
A new approach to the synthesis of the nonpeptide NOP receptor antagonist J-113397
Sulima, Agnieszka,Folk, John,Jacobson, Arthur E.,Rice, Kenner C.
, p. 1547 - 1553 (2008/02/08)
A new synthesis that eliminates the need for chromatographic separation in order to obtain multigram quantities of J-113397, a competitive antagonist of the N/OFQ-NOP receptor system, is reported. N-Benzyl protected 4-oxopiperidinecarboxylate was used as the starting material to obtain an N-benzyl intermediate that could be resolved at a relatively early stage in the synthesis. The crucial step in the synthesis was reduction of the double bond of the β-enaminoester functionality of 1-benzyl-4-(3-ethyl-2-oxo-2,3- dihydrobenzoimidazol-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester, since Pd/C reduction gave inseparable mixtures. It could be reduced and epimerized to the desired trans diastereoisomer in a one-pot reaction by treatment with magnesium metal in methanol. Georg Thieme Verlag Stuttgart.
