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Didierjean C, Marin J, Wenger E, et al. 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. Acta Crystallogr C. 2004;60:o200-3doi: 10.1107/S0108270103024053.
Didierjean, C., Marin, J., Wenger, E., Briand, J. P., Aubry, A., & Guichard, G. (2004). 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. Acta crystallographica. Section C, Crystal structure communications, 60o200-3. https://doi.org/10.1107/S0108270103024053
Didierjean, Claude, et al. "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." Acta crystallographica. Section C, Crystal structure communications vol. 60 (2004): o200-3. doi: https://doi.org/10.1107/S0108270103024053
Didierjean C, Marin J, Wenger E, Briand JP, Aubry A, Guichard G. 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. Acta Crystallogr C. 2004 Mar;60:o200-3. doi: 10.1107/S0108270103024053. Epub 2004 Feb 10. PMID: 15004383.
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Acta Crystallogr C. 2004 Mar;60:o200-3. doi: 10.1107/S0108270103024053. Epub 2004 Feb 10.

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.

Acta crystallographica. Section C, Crystal structure communications

Claude Didierjean, Julien Marin, Emmanuel Wenger, Jean Paul Briand, André Aubry, Gilles Guichard

Affiliations

  1. Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques (LCM3B), UMR No. 7036, Groupe Biocristallographie, Université Henri Poincaré, Nancy I, Faculté des Sciences,BP 239, 54506 Vandoeuvre lès Nancy CEDEX, France.

PMID: 15004383 DOI: 10.1107/S0108270103024053

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 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-H...O=C hydrogen bonds, leading to infinite chains in the crystal structure.

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