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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 13
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Original Articles

Synthesis of (R) and (S)-3-Aminoquinuclidine from 3-Quinuclidinone and (S) and (R)-1-Phenethylamine

Michel Langlois CNRS-CERCOA, 2-8 rue Henri, Dunant, F-94320, THIAIS
,
Christine Meyer CNRS-CERCOA, 2-8 rue Henri, Dunant, F-94320, THIAIS
&
Jean Louis Soulier CNRS-CERCOA, 2-8 rue Henri, Dunant, F-94320, THIAIS
Pages 1895-1911 | Accepted 26 Feb 1992, Published online: 23 Sep 2006

Citations (15)

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BruceA. Kowalczyk, JohnC. Rohloff, CharlesA. Dvorak & JohnO. Gardner. (1996) Improved Preparation of (R) and (S)-3-Aminoquinuclidine Dihydrochloride. Synthetic Communications 26:10, pages 2009-2015.
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Articles from other publishers (14)

V. A. Kondrat’ev, I. A. Yudina, A. V. Kutkin, I. V. Novikova, R. I. Novikov & Zh. V. Smirnova. (2016) Preparative method of synthesis of 1-(halomethyl)-(±)-3-quinuclidinol halides. Russian Journal of General Chemistry 86:9, pages 2135-2137.
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Yalei Zhao, Xiuling Chen, Tieqiao Chen, Yongbo Zhou, Shuang-Feng Yin & Li-Biao Han. (2014) Catalyst-Free and Selective C–N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and >P(O)H Species Affording α-Aminophosphorus Compounds. The Journal of Organic Chemistry 80:1, pages 62-69.
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Swati P. Kolet, Dipesh D. Jadhav, Balaraman Priyadarshini, Bhagyashree N. Swarge & Hirekodathakallu V. Thulasiram. (2014) Fungi mediated production and practical purification of (R)-(−)-3-quinuclidinol. Tetrahedron Letters 55:43, pages 5911-5914.
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Ganala Naga Trinadhachari, Anand Gopalkrishna Kamat, Boddu Venkata Balaji, Koilpillai Joseph Prabahar, Kolukuluru Mohan Naidu, Korupolu Raghu Babu & Paul Douglas Sanasi. (2014) An Improved Process for the Preparation of Highly Pure Solifenacin Succinate via Resolution through Diastereomeric Crystallisation. Organic Process Research & Development 18:8, pages 934-940.
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Anatoly A. Mazurov, David C. Kombo, Terry A. Hauser, Lan Miao, Gary Dull, John F. Genus, Nikolai B. Fedorov, Lisa Benson, Serguei Sidach, Yunde Xiao, Philip S. Hammond, John W. James, Craig H. Miller & Daniel Yohannes. (2012) Discovery of (2 S ,3 R )- N -[2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[ b ]furan-2-carboxamide (TC-5619), a Selective α7 Nicotinic Acetylcholine Receptor Agonist, for the Treatment of Cognitive Disorders . Journal of Medicinal Chemistry 55:22, pages 9793-9809.
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Renata Odžak & Srđanka Tomić. (2006) 3-Amidoquinuclidine derivatives: Synthesis of compounds and inhibition of butyrylcholinesterase. Bioorganic Chemistry 34:2, pages 90-98.
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Ryo Tatsumi, Kohji Seio, Masakazu Fujio, Jiro Katayama, Takashi Horikawa, Kenji Hashimoto & Hiroshi Tanaka. (2004) (+)-3-[2-(Benzo[ b ]thiophen-2-yl)-2-oxoethyl]-1-azabicyclo[2.2.2]octane as potent agonists for the α7 nicotinic acetylcholine receptor. Bioorganic & Medicinal Chemistry Letters 14:14, pages 3781-3784.
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Eusebio Juaristi, José Luis León-Romo, Adelfo Reyes & Jaime Escalante. (1999) Recent applications of α-phenylethylamine (α-PEA) in the preparation of enantiopure compounds. Part 3: α-PEA as chiral auxiliary. Part 4: α-PEA as chiral reagent in the stereodifferentiation of prochiral substrates. Tetrahedron: Asymmetry 10:13, pages 2441-2495.
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Linda Joy Brzezinski, Sara Rafel & James W. Leahy. (1997) The asymmetric Baylis-Hillman reaction as a template in organic synthesis. Tetrahedron 53:48, pages 16423-16434.
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T de Paulis, WA Hewlett, DE Schmidt, NS Mason, BL Trivedi & MH Ebert. (1997) Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues. European Journal of Medicinal Chemistry 32:5, pages 385-396.
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M Langlois, JL Soulier, V Rampillon, C Gallais, B Brémont, S Shen, D Yang, A Giudice & F Sureau. (1994) Synthesis of quinazoline-2,4-dione and naphthalimide derivatives as new 5-HT3 receptor antagonists. European Journal of Medicinal Chemistry 29:12, pages 925-940.
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M. Langlois, J.L. Soulier, M. Allainmat, S. Shen & C. Gallais. (1993) Derivatives of quinuclidine as 5-HT3 receptor antagonists: influence of an additional carbonyl group on the recognition of chirality by the receptor.. Bioorganic & Medicinal Chemistry Letters 3:8, pages 1555-1558.
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M Langlois, JL Soulier, D Yang, B Bremont, C Florac, V Rampillon & A Giudice. (1993) Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine. European Journal of Medicinal Chemistry 28:11, pages 869-880.
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M. LANGLOIS, C. MEYER & J. L. SOULIER. (2010) ChemInform Abstract: Synthesis of (R)‐ and (S)‐3‐Aminoquinuclidine (V) from 3‐ Quinuclidinone (I) and (S)‐ and (R)‐1‐Phenethylamine (II).. ChemInform 23:41.
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