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Resolution of (.+-.)-5-bromonornicotine. Synthesis of (R)- and (S)-nornicotine of high enantiomeric purity

Cite this: J. Org. Chem. 1982, 47, 21, 4165–4167
Publication Date (Print):October 1, 1982
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    This article is cited by 53 publications.

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    7. Peyton Jacob, III. Facile Pyridoxal-Catalyzed Racemization of Nornicotine and Related Compounds. The Journal of Organic Chemistry 1996, 61 (9) , 2916-2917.
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    10. C G Nwosu, C S Godin, A A Houdi, L A Damani, P A Crooks. Enantioselective Metabolism During Continuous Administration of S -(−)- and R -(+)-Nicotine Isomers to Guinea-Pigs. Journal of Pharmacy and Pharmacology 2011, 40 (12) , 862-869.
    11. Virginie Arnaud, Michel Berthelot, François‐Xavier Felpin, Jacques Lebreton, Jean‐Yves Le Questel, Jérôme Graton. Hydrogen‐Bond Accepting Strength of Five‐Membered N‐Heterocycles:The Case of Substituted Phenylpyrrolines and Myosmines. European Journal of Organic Chemistry 2009, 2009 (29) , 4939-4948.
    12. Wilfried Hatton, Virginie Silvestre, Richard J. Robins, Monique Mathé‐Allainmat, Jacques Lebreton. Synthesis of four racemic nicotine isotopomers doubly labelled with stable isotope. Journal of Labelled Compounds and Radiopharmaceuticals 2009, 52 (4) , 117-122.
    13. Yan-Qin Cheng, Zheng Bian, Chuan-Qing Kang, Hai-Quan Guo, Lian-Xun Gao. Chiral ligand 2-(2′-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes. Tetrahedron: Asymmetry 2008, 19 (13) , 1572-1575.
    14. Florence F. Wagner, Daniel L. Comins. Recent advances in the synthesis of nicotine and its derivatives. Tetrahedron 2007, 63 (34) , 8065-8082.
    15. Giorgio Chelucci. Stereoselective synthesis of optically active 1-substituted-1-pyridyl-methylamines. Tetrahedron: Asymmetry 2005, 16 (14) , 2353-2383.
    17. Kirk L. Sorgi, Cynthia A. Maryanoff, David F. McComsey, Bruce E. Maryanoff. N‐Vinylpyrrolidin‐2‐One as a 3‐Aminopropyl Carbanion Equivalent in the Synthesis of Substituted 1‐Pyrrolines: 2‐Phenyl‐1‐Pyrroline. 2003, 215-215.
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    19. Małgorzata Dukat, Imad M Damaj, Richard Young, Robert Vann, Allan C Collins, Michael J Marks, Billy R Martin, Richard A Glennon. Functional diversity among 5-substituted nicotine analogs; in vitro and in vivo investigations. European Journal of Pharmacology 2002, 435 (2-3) , 171-180.
    20. Cécile Coindet, Alain Comel, Gilbert Kirsch. Easy one-pot access to substituted 2-phenylpyrrolines from 2-pyrrolidinone. Tetrahedron Letters 2001, 42 (35) , 6101-6104.
    21. Lisa A. Peterson, Thomas E. Spratt, Weifeng Shan, Lijuan Wang, Witold Subotkowski, Robert Roth. An improved synthesis of radiolabeled 4‐(acetoxymethylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone. Journal of Labelled Compounds and Radiopharmaceuticals 2001, 44 (6) , 445-450.
    22. G.D. Byrd,, W.S. Caldwell,, B.S. Bhatti,, A. Ravard,, P.A. Crooks,. Determination of Nicotine N-1-Glucuronide, a Quaternary N-Glucuronide Conjugate, in Human Biological Samples. Drug Metabolism and Drug Interactions 2000, 16 (4) , 281-298.
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    24. Teck-Peng Loh, Jian-Rong Zhou, Xu-Ran Li, Keng-Yeow Sim. A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: stereoselective syntheses of (S)-nornicotine and 2-(2′-pyrrolidyl)-pyridines. Tetrahedron Letters 1999, 40 (44) , 7847-7850.
    25. Mui-Chiung Tsai,, John W. Gorrod,. IN VITRO METABOLISM OF (S)-(-)-[2'- 14C]NICOTINE, USING VARIOUS TISSUE PREPARATIONS OF MARMOSET. Drug Metabolism and Drug Interactions 1999, 15 (2-3) , 97-106.
    26. Jason H. Swango, Balwinder S. Bhatti, Muhammad M. Qureshi, Peter A. Crooks. A novel enantioselective synthesis of (S)-(?)- and (R)-(+)-nornicotine via alkylation of a chiral 2-hydroxy-3-pinanone ketimine template. Chirality 1999, 11 (4) , 316-318.<316::AID-CHIR9>3.0.CO;2-D
    27. Peter A. Crooks. Chemical properties of nicotine and other tobacco-related compounds. 1999, 69-147.
    28. Peyton Jacob, Gary D. Byrd. Use of gas chromatographic and mass spectrometric techniques for the determination of nicotine and its metabolites. 1999, 191-224.
    29. J. W. GORROD, Y. SAI. Recognition of novel artifacts produced during the microsomal incubation of secondary alicyclic amines in the presence of cyanide. Xenobiotica 1997, 27 (4) , 389-400.
    30. Niranjan M Deo, Peter A Crooks. Regioselective alkylation of N-(diphenylmethylidine)-3-(aminomethyl)pyridine: A simple route to minor tobacco alkaloids and related compounds. Tetrahedron Letters 1996, 37 (8) , 1137-1140.
    31. Alain Ravard, Peter A. Crooks. Chiral purity determination of tobacco alkaloids and nicotine-like compounds by1H NMR spectroscopy in the presence of 1,1?-binaphthyl-2,2?-diylphosphoric acid. Chirality 1996, 8 (4) , 295-299.<295::AID-CHIR1>3.0.CO;2-F
    32. Mark J Bamford, Mark Beard, David T Cherry, Mark G Moloney. A concise approach to functionalised, homochiral pyrrolidinones. Tetrahedron: Asymmetry 1995, 6 (2) , 337-340.
    33. H. Nybäck, C. Halldin, A. Åhlin, M. Curvall, L. Eriksson. PET studies of the uptake of (S)- and (R)-[11C]nicotine in the human brain: difficulties in visualizing specific receptor binding in vivo. Psychopharmacology 1994, 115 (1-2) , 31-36.
    34. Peyton Jacob, Lisa Yu, Gang Liang, Alexander T. Shulgin, Neal L. Benowitz. Gas chromatographic—mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. Journal of Chromatography B: Biomedical Sciences and Applications 1993, 619 (1) , 49-61.
    35. Linda P. Dwoskin, Susan T. Buxton, Ann L. Jewell, Peter A. Crooks. S (‐)‐Nornicotine Increases Dopamine Release in a Calcium‐Dependent Manner from Superfused Rat Striatal Slices. Journal of Neurochemistry 1993, 60 (6) , 2167-2174.
    36. Fuji Yokoi, Tasuku Komiyama, Takashi Ito, Tokishi Hayashi, Masaaki Iio, Toshihiko Hara. Application of carbon-11 labelled nicotine in the measurement of human cerebral blood flow and other physiological parameters. European Journal of Nuclear Medicine 1993, 20 (1) , 46-52.
    37. Christer Halldin, Kjell Någren, Carl-Gunnar Swahn, Bengt Långström, Henrik Nybäck. (S)- and (R)-[11C]nicotine and the metabolite ()-[11C]cotinine. preparation, metabolite studies and in vivo distribution in the human brain using PET. International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology 1992, 19 (8) , 871-880.
    38. J. R. Copeland, A. Adem, P. Jacob, A. Nordberg. A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Naunyn-Schmiedeberg's Archives of Pharmacology 1991, 343 (2) , 123-127.
    39. K. Takada, M. D. B. Swedberg, S. R. Goldberg, J. L. Katz. Discriminative stimulus effects of intravenous l-nicotine and nicotine analogs or metabolites in squirrel monkeys. Psychopharmacology 1989, 99 (2) , 208-212.
    40. A. Nordberg, P. Hartvig, H. Lundqvist, G. Antoni, J. Ulin, B. Långström. Uptake and regional distribution of (+)-(R)- and (−)-(S)-N-[methyl-11C]-nicotine in the brains of Rhesus monkey an attempt to study nicotinic receptors in vivo. Journal of Neural Transmission - Parkinson's Disease and Dementia Section 1989, 1 (3) , 195-205.
    41. Klaus Bernauer, François Gretillat. Stereoselectivity in Reactions of Metal Complexes. Part XI. 2,6‐Bis(pyrrolidin‐2‐yl)pyridine: Synthesis and resolution of the meso and the optically active isomers. Complex formation with copper(II) ion in aqueous solution. Helvetica Chimica Acta 1989, 72 (3) , 477-481.
    42. H. Nybäck, A. Nordberg, B. Långström, C. Halldin, P. Hartvig, A. Åhlin, C-G. Swahn, G. Sedvall. Chapter 30 Attempts to visualize nicotinic receptors in the brain of monkey and man by positron emission tomography. 1989, 313-319.
    43. Peyton Jacob, Neal L. Benowitz, Alexander T. Shulgin. Synthesis of optically pure deuterium‐labelled nicotine, nornicotine and cotinine. Journal of Labelled Compounds and Radiopharmaceuticals 1988, 25 (10) , 1117-1128.
    44. James C. Wiley, David H. T. Chien, Nancy A. Nungesser, Dorothy Lin, Stephen S. Hecht. Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring. Journal of Labelled Compounds and Radiopharmaceuticals 1988, 25 (7) , 707-716.
    45. Peyton Jacob, Neal L. Benowitz, James R. Copeland, Marcus E. Risner, Edward J. Cone. Disposition Kinetics of Nicotine and Cotinine Enantiomers in Rabbits and Beagle Dogs. Journal of Pharmaceutical Sciences 1988, 77 (5) , 396-400.
    46. Mark K. Shigenaga, Peyton Jacob, Anthony Trevor, Neal Castagnoli, Neal Benowitz. Synthesis of specifically labeled (S)‐nicotine‐5‐ 3 H and (S)‐cotinine‐5‐ 3 H BY carrier free tritiolysis of the corresponding 5‐bromo derivatives. Journal of Labelled Compounds and Radiopharmaceuticals 1987, 24 (6) , 713-723.
    47. Daniel W. Armstrong, Larry A. Spino, Soon M. Han, Jeffrey I. Seeman, Henry V. Secor. Enantiomeric resolution of racemic nicotine and nicotine analogues by microcolumn liquid chromatography with β-cyclodextrin inclusion complexes. Journal of Chromatography A 1987, 411 , 490-493.
    48. N. Khoukhi, M. Vaultier, R. Carrié. Synthesis and reactivity of methyl γ-azido butyrates and ethyl σ-azido valerates and of the corresponding acid chlorides as useful reagents for the aminoalkylation. Tetrahedron 1987, 43 (8) , 1811-1822.
    49. Ahmed Zidani, Michel Vaultier. Chelation assisted transmetallation of tetraalkyl tin derivatives: C-metallated lithiocarbamates as d3 reagents for the synthesis of δ-hydroxycarbamates.. Tetrahedron Letters 1986, 27 (7) , 857-860.
    50. Leo G. Abood, Susan Grassi, Helen D. Noggle. Comparison of the binding of optically pure (?)- and (+)-[3H]nicotine to rat brain membranes. Neurochemical Research 1985, 10 (2) , 259-267.
    51. K.C. Cundy, P.A. Crooks. High-performance liquid chromatographic method for the determination of N-methylated metabolites of nicotine. Journal of Chromatography B: Biomedical Sciences and Applications 1984, 306 , 291-301.
    52. P. III. JACOB. ChemInform Abstract: RESOLUTION OF (.+‐.)‐5‐BROMONORNICOTINE. SYNTHESIS OF (R)‐ AND (S)‐NORNICOTINE OF HIGH ENANTIOMERIC PURITY. Chemischer Informationsdienst 1983, 14 (15)
    53. K.C. Cundy, P.A. Crooks. Unexpected pehnomenon in the high-performance liquid chromatographic anlaysis of racemic 14C-labelled nicotine: Separation of enantiomers in a totally achiral system. Journal of Chromatography A 1983, 281 , 17-33.

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