Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 3 (March 2004)

Acta Cryst. (2004). C60, o200-o203 [doi:10.1107/S0108270103024053]

tert-Butyl (6S)-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate and tert-butyl (4R,6S)-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate

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

Abstract: X-ray studies reveal that tert-butyl (6S)-6-isobutyl-2,4-dioxopiperidine-1-carboxylate occurs in the 4-enol form, viz. tert-butyl (6S)-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate, C₁₄H₂₃NO₄, when crystals are grown from a mixture of dichloromethane and pentane, and has an axial orientation of the isobutyl side chain at the 6-position of the piperidine ring. Reduction of the keto functionality leads predominantly to the corresponding [beta] -hydroxylated [bold delta] -lactam, tert-butyl (4R,6S)-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate, C₁₄H₂₅NO₄, with a cis configuration of the 4-hydroxy and 6-isobutyl groups. The two compounds show similar molecular packing driven by strong O-HO=C hydrogen bonds, leading to infinite chains in the crystal structure.

Formula: C₁₄H₂₃NO₄ and C₁₄H₂₅NO₄

Online 10 February 2004


	Structure factor file (CIF format) (158.3 kbytes) Contains datablock II

	Structure factor file (CIF format) (78.7 kbytes) Contains datablock III

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