36127-17-0Relevant articles and documents
METHOD FOR THE PREPARATION OF N-MONOFLUOROALKYL TROPANES AND THEIR USE
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Page/Page column 14, (2021/07/31)
The present invention relates to a method for the preparation of an N-monofluoroalkyl tropane, a method for the preparation of a trialkyltin tropane, a method for the preparation of an iodinated and/or radioiodinated tropane and the use of the N-monofluoroalkyl tropane as a precursor in the method for the preparation of the trialkyltin tropane and/or the iodinated and/or radioiodinated tropane.
New classes of potent and bioavailable human renin inhibitors
Remen, L'ubos,Bezencon, Olivier,Richard-Bildstein, Sylvia,Bur, Daniel,Prade, Lars,Corminboeuf, Olivier,Boss, Christoph,Grisostomi, Corinna,Sifferlen, Thierry,Strickner, Panja,Hess, Patrick,Delahaye, Stephane,Treiber, Alexander,Weller, Thomas,Binkert, Christoph,Steiner, Beat,Fischli, Walter
body text, p. 6762 - 6765 (2010/06/12)
New classes of de novo designed renin inhibitors are reported. Some of these compounds display excellent in vitro and in vivo activities toward human renin in a TGR model. The synthesis of these new types of mono- and bicyclic scaffolds are reported, and properties of selected compounds discussed.
Process for producing optically active tropinonemonocarboxylic acid derivative
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, (2008/06/13)
An optically active tropinonemonocarboxylic acid ester derivative useful as an intermediate for synthesis of optically active tropane derivatives was obtained by reacting succindialdehyde with an organic amine and acetonedicarboxylic acid ester to obtain a tropinonedicarboxylic acid ester derivative, and then subjecting this derivative to enzyme-catalyzed asymmetric dealkoxy-carbonylation. Since anhydroecgonine methyl ester derived from the optically active tropinone-monocarboxylic acid ester derivative by reduction and dehydration had the same direction of optical rotation as in the case of anhydroecgonine methyl ester obtained from natural cocaine, it was proved that the obtained optically active tropinonemonocarboxylic acid ester derivative had the same absolute configuration as that of natural cocaine. The yield of the optically active tropinonemonocarboxylic acid ester derivative from the asymmetric dealkoxycarbonylation was 30 to 50 mol %, and its optical purity was 70 to 97% ee. In addition, it was found that a crystalline optically active anhydroecgonine carboxylic acid ester derivative can be obtained by reducing and then dehydrating the optically active tropinonemonocarboxylic acid ester derivative and that its optical purity can easily be increased by recrystallization.
Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]- octane-2,4-dicarboxylates using porcine liver esterase: A new route to (-)- anhydroecgonine methyl ester
Node, Manabu,Nakamura, Soichi,Nakamura, Daisaku,Katoh, Takahiro,Nishide, Kiyoharu
, p. 5357 - 5360 (2007/10/03)
The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl- 3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)-cocaine related radiopharmaceuticals such as (1R)-β-CIT, for diagnosis of Parkinson's disease.
Stereoselective deprotonation of tropinone and reactions of tropinone lithium enolate
Majewski, Marek,Zheng, Guo-Zhu
, p. 2618 - 2626 (2007/10/02)
Tropinone (6) was deprotonated with lithium diisopropylamide and with chiral lithium amides (18-24) and the resulting enolates (two enantiomers) were treated with electrophiles.The aldol reaction with benzaldehyde and deuteration were both diastereoselective.The former yielded only one isomer (exo, anti) of the aldol 8a; the latter proceeded from the exo face.This selectivity permitted us to probe the deprotonation of tropinone with lithium amides; it was concluded that the reaction involves predominantly the exo axial protons.The reaction of tropinone enolate with ethyl chloroformate led, via a ring opening, to the cycloheptenone derivative 9.The reaction with methyl cyanoformate yielded, in the presence of silver acetate and acetic acid, the β-ketoester 8b; however, in the absence of these additives, and especially when 12-crown-4 was added to the enolate, a ring opening leading to the pyrrolidine derivative 10 occured instead.Deprotonation of tropinone with chiral amides proceeded with modest enantioselectivity.A synthesis of non-racemic anhydroecgonine via this strategy allowed establishing the absolute stereochemistry of deprotonation.
Syntheses and Conformational Analyses of Isomeric Cocaines: A Proton and Carbon-13 Nuclear Magnetic Resonance Study
Carroll, F. Ivy,Coleman, Michael L.,Lewin, Anita H.
, p. 13 - 19 (2007/10/02)
The 1H and 13C NMR spectra of cocaine (1), pseudococaine (2), allococaine (3), allopseudococaine (4), and the hydrochloride salts of 1, 2, and 4 have been recorded.The conformation of the piperidine ring in all four isomers, including the orientation of the N-methyl substituent, was determined from analysis of the data.Vicinal, geminal, and long-range coupling constants strongly suggest a chair conformation for the piperidine ring of all the compounds studied.Comparison of the 1H and 13C chemical shift data suggests that 2 and 4 have a larger population of axial N-methyl substituents than 1 and 3, respectively.Improved procedures for the synthesis of 2, 3, and 4 are reported.In particular, a stereoselective route to 4 is presented.
