- Copper-catalysed selective hydroamination reactions of alkynes
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The development of selective reactions that utilize easily available and abundant precursors for the efficient synthesis of amines is a long-standing goal of chemical research. Despite the centrality of amines in a number of important research areas, including medicinal chemistry, total synthesis and materials science, a general, selective and step-efficient synthesis of amines is still needed. Here, we describe a set of mild catalytic conditions utilizing a single copper-based catalyst that enables the direct preparation of three distinct and important amine classes (enamines, ±-chiral branched alkylamines and linear alkylamines) from readily available alkyne starting materials with high levels of chemo-, regio-and stereoselectivity. This methodology was applied to the asymmetric synthesis of rivastigmine and the formal synthesis of several other pharmaceutical agents, including duloxetine, atomoxetine, fluoxetine and tolterodine.
- Shi, Shi-Liang,Buchwald, Stephen L.
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- A PROCESS FOR THE PREPARATION OF TOLTERODINE TARTRATE
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The present invention relates to provide an improved process for the preparation of tolterodine or salt thereof, comprises a step of reducing 3-(2-methoxy-5-methylphenyl) -3-phenyl propionic acid of formula (III) in the presence of a reducing agent, an acidic reagent and a solvent to obtain 3-(2-methoxy-5-methylphenyl) -3-phenyl propanol of formula (IV).
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Page/Page column 18; 10
(2010/05/13)
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- A PROCESS FOR THE PREPARATION OF TOLTERODINE TARTRATE
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The present invention relates to provide a process for the preparation of (+)-(R)-Tolterodine-L-tartrate, comprises a step of aminating hydroxyl protected 3-(2-methoxy-5-methylphenyl)-3-phenyl propanol of formula (V) with diisopropylamine in the presence of water to obtain N, N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropyl amine of formula (VI).
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Paragraph 175-182
(2010/09/03)
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- METHOD OF OBTAINING 3,3-DIPHENYLPROPYLAMINES
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The invention relates to a method of obtaining 3,3-diphenylpropylamines (I), wherein R1 is H, alkyl, haloalkyl or alkoxyalkyl, R2 is alkyl, alkoxy, halogen, NO2, CN, CHO, which may be free or protected, CH2OH or COOR6, and R3 and R4 are selected independently from H and alkyl or together with the nitrogen to which they are bound form a ring having 3 to 7 members. The inventive method consists in reacting a propylenephenylamine and a disubstituted aromatic hydrocarbon and, if necessary, separating the desired enantiomer or the mixture of enantiomers, and/or converting the compound (I) into a salt. Compounds (I) are muscarinic receptor antagonists which can be used in the treatment of urinary incontinence and other symptoms of urinary bladder hyperactivity. Said compounds include tolterodine.
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Page/Page column 11
(2008/12/05)
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- NOVEL PROCESS FOR THE PREPARATION OF TOLTERODINE
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The present invention relates to a novel and improved process for the preparation of tolterodine of formula I. Key steps involved in the process are a vinyl Grignard reaction on a benzophenone derivative of formula XXI to get the vinyl carbinol derivative
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Page/Page column 17
(2010/11/26)
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- Process for producing tolterodine
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The present invention provides a process for producing tolterodine of the formula (1) or its salt, which comprises a step reacting a compound of the formula (2) with a base to obtain a reaction product; a step reacting the reaction product with a compound
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Page/Page column 9; 9-10
(2010/11/28)
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- METHOD OF OBTAINING TOLTERODINE
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The process comprises reacting a compound of formula (II), where R is a hydroxyl protecting group, and the asterisk indicates an asymmetric carbon atom, with diisopropylamine in the presence of a reducing agent; optionally converting the resulting intermediate into a salt and, if so desired, isolating it; removing the hydroxyl protecting group; and if so desired, separating the desired (R) or (S) enantiomer, or the mixture of enantiomers and/or converting the obtained compound into a pharmaceutically acceptable salt thereof. Tolterodine is a muscarinic receptor antagonist useful in treating urinary incontinence and other symptoms of urinary bladder hyperactivity.
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Page/Page column 9-10
(2008/06/13)
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- Process for the preparation of tolterodine
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A novel process for the preparation of tolterodine, i.e. (R)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine, in the racemic form, as well as intermediates useful for its preparation.
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Page/Page column 5-6
(2008/06/13)
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- A process for the preparation of tolterodine
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A novel process for the preparation of tolterodine (I), i.e. (R)-N,N-diisopropyI-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine, in the racemic form, as well as intermediates useful for its preparation.
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Page/Page column 8-9
(2010/11/23)
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- Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine
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A process is described for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine comprising substitution of the sulfonyloxy group of the compound of the formula in which the substituents R and R″ have the meanings stated in the description, in a solvent comprising an ionic liquid, to yield the tertiary amine of the formula and the subsequent deprotection thereof.
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Page/Page column 8
(2008/06/13)
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- TOLTERODINE, COMPOSITIONS AND USES THEREOF, AND PREPARATION OF THE SAME
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Racemic tolterodine free base in crystalline form, tolterodine with improved purity, compositions and uses thereof, and processes of preparing the same.
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Page/Page column 13
(2008/06/13)
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- Method for producing 3,3-diarylpropylamines
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The invention relates to a novel method for producing 3,3-diarylpropylamines of formula (I), wherein A represents a substituted or unsubstituted aryl radical, X represents H, OH or OR3 and Y, R1, R2 and R3 have
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- 3,3-DIPHENYLPROPYLAMINES AND PHARMACEUTICAL COMPOSITIONS THEREOF
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Novel 3,3-diphenylpropylamines of formula (I) wherein R1 signifies hydrogen or methyl, R2, R3 and R4 independently signify hydrogen, methyl, methoxy, hydroxy, carbamoyl, sulphanoyl or halogen, and X represents a tertiary amino group -NR5, R6, wherein R5 and R6 signify non-aromatic hydrocarbyl groups, which may be the same or different and which together contain at least three carbon atoms, and which may form a ring together with the amine nitrogen, their salts with physiologically acceptable acids and, when the compounds can be in the form of optical isomers, the racemic mixture and the individual enantiomers, their use as drugs, especially as anticholinergic agents, their use for preparing an anticholinergic drug, pharmaceutical compositions containing the novel amines, and methods for preparing the same
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