Advertisement

Chemical Papers

, Volume 73, Issue 2, pp 535–542 | Cite as

An efficient synthesis of N-tert-butyl amides by the reaction of tert-butyl benzoate with nitriles catalyzed by Zn(ClO4)2·6H2O

  • Cheng-Liang Feng
  • Bin Yan
  • Min Zhang
  • Jun-Qing Chen
  • Min JiEmail author
Short Communication
  • 15 Downloads

Abstract

An efficient, mild and inexpensive synthesis of N-tert-butyl amides from the reaction of nitriles (aryl, benzyl and sec-alkyl nitriles) with tert-butyl benzoate catalyzed by the employment of 2 mol% Zn(ClO4)2·6H2O at 50 °C under the solvent-free conditions is described. The reaction with aryl nitriles was carried out well and afforded the N-tert-butyl amides in 87–97% yields after 1 h. The benzyl and sec-alkyl nitriles also proceeded well and produced the N-tert-butyl amides in 83–91% yields after 5 h.

Keywords

Ritter reaction Tert-butyl benzoate Zn(ClO4)2·6H2Amides Solvent-free 

Notes

Acknowledgements

We are grateful to Nantong City Science Foundation (No. 2015) and Science program of Jiangsu College of Engineering and Technology for financial support.

Supplementary material

11696_2018_586_MOESM1_ESM.docx (1.7 mb)
Supplementary material 1 (DOCX 1733 kb)

References

  1. Ahmed TA, Al-Abd AM (2018) Effect of finasteride particle size reduction on its pharmacokinetic, tissue distribution and cellular permeation. Drug Deliv 25:555–563.  https://doi.org/10.1080/10717544.2018.1440446 CrossRefGoogle Scholar
  2. Baine NH, Owings FF, Kline DN, Resnick T, Ping LJ, Fox M, Mewshaw RE, Tickner AM, Kowalski CJ (1994) Improved syntheses of epristeride, a potent human 5.alpha.-reductase inhibitor. J Org Chem 59:5987–5989.  https://doi.org/10.1021/jo00099a031 CrossRefGoogle Scholar
  3. Baum JC, Milne JE, Murry JA, Thiel OR (2009) An efficient and scalable ritter reaction for the synthesis of tert-butyl amides. J Org Chem 74:2207–2209.  https://doi.org/10.1021/jo8024797 CrossRefGoogle Scholar
  4. Callens E, Burton AJ, Barrett AGM (2006) Synthesis of amides using the Ritter reaction with bismuth triflate catalysis. Tetrahedron Lett 47:8699–8701.  https://doi.org/10.1016/j.tetlet.2006.10.02317 CrossRefGoogle Scholar
  5. Chang JWW, Ton TMU, Tania S, Taylor PC, Chan PW (2010) Practical copper(I)-catalysed amidation of aldehydes. Chem Commun 46:922–924.  https://doi.org/10.1039/b918588g CrossRefGoogle Scholar
  6. Clayden J, Hebditch KR, Read B, Helliwell M (2007) Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids. Tetrahedron Lett 48:8550–8553.  https://doi.org/10.1016/j.tetlet.2007.09.150 CrossRefGoogle Scholar
  7. Ghosh AK, Hussain KA, Fidanze S (1997) Asymmetric aldol route to hydroxyethylamine isostere: stereoselective synthesis of the core unit of saquinavir. J Org Chem 62:6080–6082.  https://doi.org/10.1021/jo9706943 CrossRefGoogle Scholar
  8. Gololobov YG, Kasukhin LF (1992) Recent advances in the Staudinger reaction. Tetrahedron 48:1353–1406.  https://doi.org/10.1016/S0040-4020(01)92229-X CrossRefGoogle Scholar
  9. Hazarika N, Baishya G (2014) One-pot sequential Schmidt and Ritter reactions for the synthesis of N-tert-butyl amides. Eur J Org Chem 2014:5686–5690.  https://doi.org/10.1002/ejoc.201402662 CrossRefGoogle Scholar
  10. Hensley K, Robinson KA, Pye QN, Floyda RA, Cheng I, Garland WA, Irwin I (2000) CPI-1189 inhibits interleukin 1b-induced p38-mitogen-activated protein kinase phosphorylation: an explanation for its neuroprotective properties? Neurosci Lett 281:179–182.  https://doi.org/10.1016/S0304-3940(00)00861-2 CrossRefGoogle Scholar
  11. Indalkar KS, Khatri CK, Chaturbhuj GU (2017) Sulfated polyborate: a mild, efficient catalyst for synthesis of N-tert-butyl/N-trityl protected amides via Ritter reaction. J Chem Sci 129:415–420.  https://doi.org/10.1007/s12039-017-1257-7 CrossRefGoogle Scholar
  12. Jiang H, Liu B, Li Y, Wang A, Huang H (2011) Synthesis of amides via palladium-catalyzed amidation of aryl halides. Org Lett 13:1028–1031.  https://doi.org/10.1021/ol103081y CrossRefGoogle Scholar
  13. Jiang D, He T, Ma L, Wang Z (2014) Recent developments in Ritter reaction. RSC Adv 4:64936–64946.  https://doi.org/10.1039/c4ra10784e CrossRefGoogle Scholar
  14. Krabbe SW, Chan VS, Franczyk TS, Shekhar S, Napolitano JG, Presto CA, Simanis JA (2016) Copper-catalyzed aerobic oxidative amidation of benzyl alcohols. J Org Chem 81:10688–10697.  https://doi.org/10.1021/acs.joc.6b01686 CrossRefGoogle Scholar
  15. Lang S, Murphy JA (2006) Azide rearrangements in electron-deficient systems. Chem Soc Rev 35:146–156.  https://doi.org/10.1039/b505080d CrossRefGoogle Scholar
  16. Larsen J, Jørgensen KA, Christensen D (1991) Duality of the permanganate ion in the oxidation of imines. oxidation of lmines to amides. J Chem Soc Perkin Trans 1(1991):1187–1190.  https://doi.org/10.1039/P19910001187 CrossRefGoogle Scholar
  17. Mao J, Shen Y, Cao C, Shu Z, Zheng L, Xu X (2017) Preparation of finasteride via oxidative elimination of 2-iododihydrofinasteride by using peroxydisulfates as oxidizing agents. Chin J Org Chem 37:2430–2434.  https://doi.org/10.6023/cjoc201704009 CrossRefGoogle Scholar
  18. Qu GR, Song YW, Niu HY, Guo HM, Fossey JS (2012) Cu(OTf)2-catalysed Ritter reaction: efficient synthesis of amides from nitriles and halohydrocarbons in water. RSC Adv 2:6161–6163.  https://doi.org/10.1039/c2ra20941a CrossRefGoogle Scholar
  19. Rossen K, Weissman SA, Sager J, Reamer RA, Askin D, Volante RP, Reider PJ (1995) Asymmetric hydrogenation of tetrahydropyrazines: synthesis of (S)-piperazine-2-tert-butyl- carboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir. Terrahedron Lett 36:6419–6422.  https://doi.org/10.1016/0040-4039(95)01345-I CrossRefGoogle Scholar
  20. Sanchez CG, Molinski SV, Gongora R, Sosulski M, Fuselier T, MacKinnon SS, Mondal D, Lasky JA (2018) The antiretroviral agent nelfinavir mesylate. Arthritis Rheumatol 70:115–126.  https://doi.org/10.1002/art.40326 CrossRefGoogle Scholar
  21. Tamaddon F, Tavakoli F (2011) One-pot synthesis of N-tert-butyl amides from alcohols, ethers and esters using ZnCl2/SiO2 as a recyclable heterogeneous catalyst. J Mol Catal A Chem 337:52–55.  https://doi.org/10.1016/j.molcata.2011.01.013 CrossRefGoogle Scholar
  22. Valeur E, Bradley M (2009) Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev 38:606–631.  https://doi.org/10.1039/B701677H CrossRefGoogle Scholar
  23. Wannberg J, Larhed M (2003) Increasing rates and scope of reactions: sluggish amines in microwave-heated aminocarbonylation reactions under air. J Org Chem 68:5750–5753.  https://doi.org/10.1021/jo034382d CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Institute of Pharmaceutical EngineeringJiangsu College of Engineering and TechnologyNantongPeople’s Republic of China
  2. 2.School of Biological Sciences and Medical EngineeringSoutheast UniversityNanjingPeople’s Republic of China

Personalised recommendations