Skip to main content
SpringerLink
Log in

Facile syntheses of isotope-labeled chiral octahydroindole-2-carboxylic acid and its N-methyl analog

  • Published:
Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

We have synthesized deuterium and carbon-14 labeled enantiomerically pure octahydroindole-2-carboxylic acid (PD0140417), N-methyl octahydroindole-2-carboxylic acid (PD0348183) and their racemic analogs (PD0108405 and PD0338055). [ring-U-14C]PD0140417 was prepared from [ring-U-14C]benzoic acid in a seven-step synthesis in 6.2% overall radiochemical yield. [14C]PD0348183 was prepared from [14C]BaCO3 in a five-step synthesis in 16% radiochemical yield. Additionally, [D]PD0108405 and [D]PD0338055 were synthesized by direct platinum-catalyzed hydrogenation with deuterium gas.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Altatorre-Santamaria S, Rodriguez-Mata M (2008) Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution. Tetrahedron Asymmetry 19(14):1714–1719

    Article  Google Scholar 

  2. Pyne SG, Javidan A (1995) Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one. Tetrahedron 51(17):5157–5168

    Article  CAS  Google Scholar 

  3. Henning R, Urbach H (1983) Diastereoselective synthesis of bicyclic amino acids via ring contraction of α-chlorolactams. Tetrahedron Lett 24(48):5339–5342

    Article  CAS  Google Scholar 

  4. Blankley CJ, Kaltenbronn JS, DeJohn DE, Werner A, Bennett LR, Bobowski G (1987) Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids. J Med Chem 30:992–998

    Article  CAS  Google Scholar 

  5. Chen CY, Lieberman DR, Larsen RD, Verhoeven TR, Reider PJ (1997) Synthesis of indoles via a palladium-catalyzed annulations between iodoanilines and ketones. J Org Chem 62:2676–2677

    Article  CAS  Google Scholar 

  6. Muchowski JM, Venuti MC (1980) Ortho functionalization of N-(tert-butoxycarbonyl) aniline. J Org Chem 45(23):4798–4801

    Article  CAS  Google Scholar 

  7. Kelly TA, McNeil DW (1994) A simple method for the protection of aryl amines as their t-butylcarbamoyl derivatives. Tetrahedron Lett 35(48):9003–9006

    Article  CAS  Google Scholar 

  8. Kondo Y, Kojima S, Sakamoto T (1997) General and facile synthesis of indole with oxygen-bearing substituents at the benzene moiety. J Org Chem 62:6507–6511

    Article  CAS  Google Scholar 

  9. Sayago FJ, Calaza MI, Jimenez AI, Cativiela C (2008) Versatile methodology for the synthesis and functionalization of (2R, 3aS, 7aS)-octahydroindole-2-carboxylic acid. Tetrahedron 64:84–91

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The author thanks Dr. Laura Greenfield and Dr. Che Huang for helpful discussion during the implementation of this project.

Author information

Authors and Affiliations

  1. Radiochemistry Group, Chemical R&D, Groton Lab. Pfizer, Inc, 5 Tanglewood Dr. East Lyme, CT, 06333, USA

    Yinsheng Zhang

Authors
  1. Yinsheng Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yinsheng Zhang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhang, Y. Facile syntheses of isotope-labeled chiral octahydroindole-2-carboxylic acid and its N-methyl analog. J Radioanal Nucl Chem 292, 1371–1376 (2012). https://doi.org/10.1007/s10967-012-1619-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10967-012-1619-z

Keywords

Search

Navigation