A new synthetic route for the preparation of pregabalin

References

• (a) Bassas, O.; Huuskonen, J.; Rissanen, K.; Koskinen, A. M. P. Eur. J. Org. Chem. 2009, 9, 1340–1351. DOI: 10.1002/ejoc.200801220.
   Web of Science ®Google Scholar
  (b) Calandre, E. P.; Rico - Villademoros, F.; Slim, M. Alpha2delta Ligands, Gabapentin, Pregabalin and Mirogabalin: A Review of Their Clinical Pharmacology and Therapeutic Use. Expert Rev. Neurother. 2016, 16, 1263–1277. DOI: 10.1080/14737175.2016.1202764.
   PubMed Web of Science ®Google Scholar
  (c) Tassone, D. M.; Boyce, E.; Guyer, J.; Nuzum, D. Pregabalin: A Novel γ-Aminobutyric Acid Analogue in the Treatment of Neuropathic Pain, Partial-Onset Seizures, and Anxiety Disorders. Clin. Ther. 2007, 29, 26–48. DOI: 10.1016/j.2007.01.013.
   PubMed Web of Science ®Google Scholar
  (d) Wayne, H.; Richard, A.; Christopher, E. Sleep 2012, 35, 1039–1062.;
   PubMed Web of Science ®Google Scholar
  (f) Lauria-Horner, B. A.; Pohl, R. B. Pregabalin: A New Anxiolytic. Expert Opin Investig Drugs 2003, 12, 663–672. DOI: 10.1517/13543784.12.4.663.
   PubMed Web of Science ®Google Scholar
  (g) Shneker, B. F.; McAuley, J. W. Pregabalin: A New Neuromodulator with Broad Therapeutic Indications. Ann. Pharmacother. 2005, 39, 2029–2037. DOI: 10.1345/aph.1G078.
   PubMed Web of Science ®Google Scholar
• Hoekstra, M. S.; Sobieray, D. M.; Schwindt, M. A.; Mulhern, T. A.; Grote, T. M.; Huckabee, B. K.; Hendrickson, V. S.; Franklin, L. C.; Granger, E. J.; Karrick, G. L. Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant. Org. Process Res. Dev. 1997, 1, 26–38. DOI: 10.1021/op9600320.
   Web of Science ®Google Scholar
• (a) Sammis, G. M.; Jacobsen, E. N. Highly Enantioselective, Catalytic Conjugate Addition of Cyanide to Alpha, Beta-Unsaturated Imides. J. Am. Chem. Soc. 2003, 125, 4442–4443. DOI: 10.1021/ja034635k.
   PubMed Web of Science ®Google Scholar
  (b) Burk, M. J.; de Koning, P. D.; Grote, T. M.; Hoekstra, M. S.; Hoge, G.; Jennings, R. A.; Kissel, W. S.; Le, T. V.; Lennon, I. C.; Mulhern, T. A.; et al. An Enantioselective Synthesis of (S)-(+)-3-Aminomethyl-5-Methylhexanoic Acid via Asymmetric Hydrogenation. J. Org. Chem. 2003, 68, 5731–5734. DOI: 10.1021/jo034397b.
   PubMed Web of Science ®Google Scholar
  (c) Hoge, G. Synthesis of Both Enantiomers of a P-Chirogenic 1,2-Bisphospholanoethane Ligand via Convergent Routes and Application to Rhodium-Catalyzed Asymmetric Hydrogenation of CI-1008 (Pregabalin). J. Am. Chem. Soc. 2003, 125, 10219–10227. DOI: 10.1021/ja034715o.
   PubMed Web of Science ®Google Scholar
• (a) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. Asymmetric Synthesis of Calyculin A. 2. The C26-C37.gamma.-Amino Acid Fragments. J. Org. Chem. 1992, 57, 1961–1963. DOI: 10.1021/jo00033a010.
   Web of Science ®Google Scholar
  (b) Brenner, M.; Seebach, D. Enantioselective Preparation of γ-Amino Acids and γ-Lactams from Nitro Olefins and Carboxylic Acids, with the Valine-Derived 4-Isopropyl-5,5-Diphenyl-1,3-Oxazolidin-2-One as an Auxiliary. HCA 1999, 82, 2365–2379. DOI: 10.1002/(SICI)1522-2675(19991215)82:12<2365::AID-HLCA2365>3.0.CO;2-#.
   Web of Science ®Google Scholar
  (c) Williams, D. R.; Kissel, W. S.; Li, J. J. Diastereoselection in the Conjugate Additions of Organocopper Reagents to N-Enoyloxazolidinones. Tetrahedron Lett. 1998, 39, 8593–8596. DOI: 10.1016/S0040-4039(9 8)01966-2.
   Web of Science ®Google Scholar
• Armstrong, A.; Convine, N.; Popkin, M. Diastereoselective Conjugate Addition of Cyanide to α,β-Unsaturated ­Oxazolidinones: Enantioselective Synthesis of ent -Pregabalin and Baclofen. Synlett 2006, 2006, 1589–1591. DOI: 10.1055/s-2006-941584.
   Web of Science ®Google Scholar
• Tovar-Gudiño, E.; Morales-Nava, R.; Fernández-Zertuche, M. Diasteroselective Conjugate Addition of Diethylaluminum Cyanide to a Conjugated N -Enoyl System: An Alternative Synthesis of (S)-Pregabalin. Can. J. Chem. 2014, 92, 45–48. DOI: 10.1139/cjc-2013-0397.
   Web of Science ®Google Scholar
• (a) Corey, E. J.; Zhang, F.-Y. Enantioselective Michael Addition of Nitromethane to α,β-Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (R)-Baclofen. Org. Lett. 2000, 2, 4257–4259. DOI: 10.1021/ol0068344.
   PubMed Web of Science ®Google Scholar
  (b) Kim, D. Y.; Huh, S. C. Enantioselective Michael Reaction of Nitroalkanes and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts. Tetrahedron 2001, 57, 8933–8989. DOI: 10.1016/s0040-4020 (01)00891-2.
   Web of Science ®Google Scholar