tert -Butyl (6 S )-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate and tert -butyl (4 R ,6 S )-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate - Université de Lorraine Access content directly
Journal Articles Acta Crystallographica Section C : Crystal Structure Communications [1968-2013] Year : 2004

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

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.

Dates and versions

hal-03996233 , version 1 (19-02-2023)

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Cite

Claude Didierjean, Julien Marin, Emmanuel Wenger, Jean-Paul Briand, André Aubry, et al.. tert -Butyl (6 S )-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate and tert -butyl (4 R ,6 S )-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate. Acta Crystallographica Section C : Crystal Structure Communications [1968-2013], 2004, 60 (3), pp.o200-o203. ⟨10.1107/S0108270103024053⟩. ⟨hal-03996233⟩
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