Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 3 (March 2004)

Acta Cryst. (2004). C60, o204-o207 [doi:10.1107/S0108270103024065]

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

C. Didierjean, J. Marin, E. Wenger, J.-P. Briand, A. Aubry and G. Guichard

Abstract: 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 (8) hydrogen-bond motif between adjacent amide groups.

Formula: C₉H₁₇NO₂ and C₉H₁₅NO₂

Online 10 February 2004


	Structure factor file (CIF format) (94.4 kbytes) Contains datablock II

	Structure factor file (CIF format) (105.7 kbytes) Contains datablock III/IV

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