- Synthesis of 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine via oxidative cleavage and reductive amination strategies
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Preparations of 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine (5) from benzonorbornadiene (1) by oxidative cleavage and reductive amination sequences were investigated. Osmium-mediated dihydroxylation of 1 followed by NaIO 4 cleavage, reductive amination and debenzylation provides 5 in 64-73% yield overall in three operations. A tandem ozonolysis-reductive amination procedure gives 5 as the tosylate salt from benzonorbornadiene with no isolation of intermediates in 28% yield.
- Brooks, Paige R.,Caron, Stephane,Coe, Jotham W.,Ng, Karl K.,Singer, Robert A.,Vazquez, Enrique,Vetelino, Michael G.,Watson Jr., Harry H.,Whritenour, David C.,Wirtz, Michael C.
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- PROCESS FOR PREPARING VARENICLINE, VARENICLINE INTERMEDIATES, AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF
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Provided herein is an improved, convenient, commercially viable and environmentally friendly process for the preparation of varenicline or a pharmaceutically acceptable salt thereof comprising reacting l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien- 10-yl)-2,2,2-trifluoro-ethanone with chloroacetaldehyde in the pressence of an oxygen source. Provided further herein is an improved and industrially advantageous process for the preparation of l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien-10-yl)-2,2,2- trifluoro-ethanone.
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Page/Page column 15-16
(2010/04/06)
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- Process for preparing varenicline and intermediates for use therein
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The present invention relates to an improved process for preparing varenicline, or pharmaceutically acceptable salts or solvates thereof, and in particular an improved process for preparing varenicline, or pharmaceutically acceptable salts or solvates thereof, employing intermediate compounds 1,2,3,4-tetrahydro-1,4-methano-naphthalene-cis-2,3-diol (a compound of Formula III), and / or indane-1,3-dicarbaldehyde (a compound of Formula IV) as prepared by a process of the present invention.
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Page/Page column 10
(2010/07/10)
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- PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF
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The invention provides an improved process for the preparation and purification of Varenicline and intermediates for the preparation of Varenicline.
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Page/Page column 8-9
(2009/12/28)
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- Aryl fused azapolycyclic compounds
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Compounds of the formula and their pharmaceutically acceptable salts, wherein R1, R2, and R3are as defined herein; intermediates for the synthesis of such compounds, pharmaceutical compositions containing such compounds; a
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- Aryl fused azapolycyclic compounds
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Compounds of the formula and their pharmaceutically acceptable salts, wherein R1, R2, R3 and n are defined as in the specification, intermediates in the synthesis of such compounds, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of neurological and psychological disorders are claimed.
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