Process for preparing dioxoazabicyclohexanes

Details Process for preparing dioxoazabicyclohexanes Process for preparing dioxoazabicyclohexanes

C - Chemistry, Metallurgy

07

D

C07D 209/52 (2006.01)

Patent

CA 2231590

A process for preparing a compound of formula (I) wherein R is C1-C6 alkyl, C3- C6 cycloalkyl or benzyl, and wherein the phenyl moiety of said benzyl group is optionally substituted by one or more substituents each independently selected from halo, nitro, C1-C6 alkyl, C1-C6 alkoxy, amino and trifluoromethyl, which comprises adding a solution comprising a compound of formula (II), a halonitromethane and an organic solvent selected from acetone, dimethylformamide, dimethylacetamide, acetonitrile, dimethylsulfoxide, N- methylpyrrolidinone and dimethoxyethane. In formula (II), wherein R is as defined above, to a mixture comprising a base and an organic solvent, said organic solvent being as defined above and the said base being selected from potassium carbonate, sodium carbonate, cesium carbonate, trisodium phosphate, and potassium fluoride, so that a compound of formula (I) is produced, any excess base being eliminated from the reaction mixture prior to recovery of the product (I).

L'invention concerne un procédé pour préparer un composé de la formule (I). Dans cette formule, R est C¿1?-C¿6? alkyle, C¿3?-C¿6? cycloalkyle ou benzyle, où le groupe phényle du groupe benzyle peut porter un ou plusieurs substituants choisis séparément parmi halo, nitro, C¿1?-C¿6? alkyle, C¿1?-C¿6? alcoxy, amino et trifluorométhyle. Le procédé consiste à préparer une solution d'un composé de la formule (II) et de halonitrométhane, dans un solvant organique choisi parmi l'acétone, diméthylformamide, diméthylacétamide, acétonitrile, diméthylsulfoxyde, N-méthylpyrrolidinone et diméthoxyéthane. Dans la formule (II), R est comme défini ci-dessus. Cette solution est ajoutée à un mélange comprenant une base et un solvant organique, ce solvant organique étant comme défini ci-dessus et la base étant choisie parmi le carbonate de potassium, le carbonate de sodium, le carbonate de césium, le phosphate trisodique et le fluorure de potassium, pour former le composé de la formule (I), l'excès éventuel de base étant éliminé du mélange réactionnel avant que le produit (I) soit récupéré.

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