207679-81-0Relevant articles and documents
Electrochemical oxidation of 5-hydroxymethyl tolterodine and identification of its oxidation products using liquid chromatography and mass spectrometry
Ku?erová, Pavla,Skopalová, Jana,Ku?era, Luká?,Táborsky, Jakub,?vecová, Hana,Lemr, Karel,Canka?, Petr,Barták, Petr
, p. 617 - 625 (2016)
The electrochemical behavior of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of antimuscarinic drugs tolterodine and fesoterodine used to treat urge incontinence and overactive bladder, was investigated using cyclic and differential pulse voltammetry at glassy carbon electrode. Electrooxidation of 5-HMT proceeds as a complex pH-dependent process. Controlled potential electrolysis of 5-HMT solutions was performed at platinum gauze electrode in aqueous-methanolic media. Electrolyzed solutions were analyzed using ultra performance liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry. Two main oxidation centers of the studied molecule were located: the p-hydroxybenzyl alcohol group and the tertiary amino group. Oxidation of the first center proceeds in several steps leading to the formation of 5-formyl tolterodine, p-benzoquinone derivative and several dimeric, hydroxylated and methoxylated products depending on pH of the solution and electrode potential. The second center is oxidized preferentially in alkaline media at higher potentials under the hydrolytic cleavage of diisopropylamine and formation of corresponding aldehydes. Mechanism of the electrochemical oxidation of 5-HMT has been proposed.
Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides
Chen, Ming,Hartwig, John F.
supporting information, p. 13972 - 13979 (2016/01/15)
The enol silanes of vinylogous esters and amides are classic dienes for Diels-Alder reactions. Here, we report their reactivity as nucleophiles in Ir-catalyzed, enantioselective allylic substitution reactions. A variety of allylic carbonates react with these nucleophiles to give allylated products in good yields with high enantioselectivities and excellent branched-to-linear ratios. These reactions occur with KF or alkoxide as the additive, but mechanistic studies suggest that these additives do not activate the enol silanes. Instead, they serve as bases to promote the cyclometalation to generate the active Ir catalyst. The carbonate anion, which was generated from the oxidative addition of the allylic carbonate, likely activates the enol silanes to trigger their activity as nucleophiles for reactions with the allyliridium electrophile. The synthetic utility of this method was illustrated by the synthesis of the anti-muscarinic drug, fesoterodine.
PROCESS FOR THE PREPARATION OF OPTICALLY PURE FESOTERODINE DERIVATIVES
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, (2015/04/15)
3,3-diphenylpropylamines of general formula (I), particularly Fesoterodine, as well as their enantiomers, solvates and salts, can be produced by treating a compound of formula (II) with a chiral alcohol to yield the diastereomeric esters of formula (IV) and (IV′), which can be further transformed into a compound of formula (I), or an enantiomer, solvate or salt thereof, wherein R1 is C1-C8 alkyl; and R2 and R3, independently of one another, represent H or C1-C6 alkyl, or together form a ring of 3 to 7 members with the nitrogen to which they are bound.
