(6 S )-6-Isobutylpiperidine-2,4-dione and (4 R ,6 S )/(4 S ,6 S )-4-hydroxy-6-isobutylpiperidin-2-one - Université de Lorraine Accéder directement au contenu
Article Dans Une Revue Acta Crystallographica Section C : Crystal Structure Communications [1968-2013] Année : 2004

(6 S )-6-Isobutylpiperidine-2,4-dione and (4 R ,6 S )/(4 S ,6 S )-4-hydroxy-6-isobutylpiperidin-2-one

Résumé

The crystal structure of (6S)-6-iso­butyl­piperidine-2,4-dione, C9H15NO2, shows that the keto tautomer is favoured in the solid state. The reduction of the keto functionality leads to the corresponding 4-hydroxy-6-iso­butyl­piperidin-2-one, C9H17NO2, with an 84:16 cis/trans ratio, containing the 4R,6S and 4S,6S isomers; the ratio of the two isomers was determined by NMR analysis of the reaction mixture. Crystals obtained from the mixture of both isomers have been studied and shown to contain the isomers in a 86:14 ratio. Hence, both X-ray and NMR analyses show that crystallization does not select the major diastereomer formed by the reduction. In both crystal structures, the two independent mol­ecules dimerize through an R_2^2(8) hydrogen-bond motif between adjacent amide groups.

Dates et versions

hal-03996022 , version 1 (19-02-2023)

Identifiants

Citer

Claude Didierjean, Julien Marin, Emmanuel Wenger, Jean-Paul Briand, André Aubry, et al.. (6 S )-6-Isobutylpiperidine-2,4-dione and (4 R ,6 S )/(4 S ,6 S )-4-hydroxy-6-isobutylpiperidin-2-one. Acta Crystallographica Section C : Crystal Structure Communications [1968-2013], 2004, 60 (3), pp.o204-o207. ⟨10.1107/S0108270103024065⟩. ⟨hal-03996022⟩
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