Crystal structure of (1R,4R)-tert-butyl 3-oxo-2-oxa-5-aza-bicyclo-[2.2.2]octane-5-carboxyl-ate.

Suvratha Krishnamurthy,Akihiko Tsuge,Tetsuji Moriguchi,Venkataprasad Jalli,Tarun Chand Vagvala

doi:10.1107/s2056989015010476

Suvratha Krishnamurthy, Akihiko Tsuge + Show 3 more

Open Access

https://doi.org/10.1107/s2056989015010476

Copy DOI

Abstract

In the title compound, C11H17NO4, commonly known as N-tert-butoxycarbonyl-5-hydroxy-d-pipecolic acid lactone, the absolute configuration is (1R,4R) due to the enantiomeric purity of the starting material which remains unchanged during the course of the reaction. In the crystal there no intermolecular hydrogen bonds.

Highlights

C11H17NO4, commonly known as Ntert-butoxycarbonyl-5-hydroxy-d-pipecolic acid lactone, the absolute configuration is (1R,4R) due to the enantiomeric purity of the starting material which remains unchanged during the course of the reaction
5-Hydroxypipecolic acid is a higher homologue of 4-hydroxyproline, which is found in dates (Witkop & Foltz, 1957). 4Hydroxyproline is formed by post-translational modification of proline in collagen and is responsible for enhancing its stability
Literature reports the synthesis of 5-hydroxypipecolic acid derivatives (Hoarau et al, 1996; Sun et al, 2008), generally forming diastereomeric mixtures of cis- and trans-5-hydroxypipecolic acids

Summary

Introduction

C11H17NO4, commonly known as Ntert-butoxycarbonyl-5-hydroxy-d-pipecolic acid lactone, the absolute configuration is (1R,4R) due to the enantiomeric purity of the starting material which remains unchanged during the course of the reaction. H-atom parameters constrained max = 0.24 e Å 3 For background information on 5-hydroxypipecolic acid and related compounds, see: Witkop & Foltz (1957); Hoarau et al. For the synthesis of a related compound, see: Krishnamurthy et al (2014).

Results

Conclusion