A new synthetic approach to 1-[(3R, 4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1, 3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide …

…, C Trapella, I Peretto, S Ronzoni, GAM Giardina

Index: De Risi, Carmela; Piero Pollini, Gian; Trapella, Claudio; Peretto, Ilaria; Ronzoni, Silvano; Giardina, Giuseppe A.M. Bioorganic and Medicinal Chemistry, 2001 , vol. 9, # 7 p. 1871 - 1877

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Citation Number: 37

Abstract

An efficient approach to 1-[(3R, 4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl- 1, 3-dihydro-benzimidazol-2-one (J-113397) 1, the first non-peptide ORL-1 receptor antagonist described in literature, is outlined. After construction of the piperidine framework through Dieckmann cyclization of the Michael adduct 8 of cyclooctylmethylamine to methyl acrylate, condensation with o-phenylendiamine produced the β-enamino ester 2, which ...