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Quality Control of (R)-(+)-Tolterodine

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(R)-(+)-Tolterodine Dilution Calculator

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Chemical Properties of (R)-(+)-Tolterodine

Cas No. 124937-51-5 SDF Download SDF
Chemical Name 2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
SMILES CC(C)N(CC[C@@H](c1ccccc1)c2cc(C)ccc2O)C(C)C
Standard InChI InChI=1S/C22H31NO/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24/h6-12,15-17,20,24H,13-14H2,1-5H3/t20-/m0/s1
Formula C22H31NO M.Wt 325.49
Solubility Soluble in DMSO
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of (R)-(+)-Tolterodine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0723 mL 15.3615 mL 30.7229 mL 61.4458 mL 76.8073 mL
5 mM 0.6145 mL 3.0723 mL 6.1446 mL 12.2892 mL 15.3615 mL
10 mM 0.3072 mL 1.5361 mL 3.0723 mL 6.1446 mL 7.6807 mL
50 mM 0.0614 mL 0.3072 mL 0.6145 mL 1.2289 mL 1.5361 mL
100 mM 0.0307 mL 0.1536 mL 0.3072 mL 0.6145 mL 0.7681 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Background on (R)-(+)-Tolterodine

Tolterodine is a potent muscarinic receptor antagonists that show selectivity for the urinary bladder over salivary glands in vivo.

References on (R)-(+)-Tolterodine

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation-protodeboronation methodology.[Pubmed: 23750041]

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation-protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.

Enantiomeric separation of R,S-tolterodine and R,S-methoxytolterodine with negatively charged cyclodextrins by capillary electrophoresis.[Pubmed: 23424041]

The methods for separation of R,S-tolterodine and R,S-methoxytolterodine enantiomers using sulfated α-, β-CD and phosphated-γ-CD by CE in acidic BGE based on Tris/phosphate pH 2.5 buffer were developed. Sulfated α- and β-CD allow anodic detection while phosphated-γ-CD allows only cathodic detection of the separated enantiomers. The influence of chiral selector (CS)'s concentration as well as the influence of composition and concentration of BGE on resolutions were studied. Reversal migration order of tolterodine and methoxytolterodine enantiomers was observed, when sulfated-α- and sulfated-β-CD were used. The developed methods with all three studied CSs, were validated and compared. All proposed methods enable determination of 0.2% of S-tolterodine as an optical impurity in pills, however the method with phosphated-γ-CD provided lower detection limit, better repeatability of peak areas and migration times, and also lower consumption of CS. Developed method employing phosphated-γ-CD that was applied for the determination of optical purity of R-tolterodine in commercial pills.

Coumarins from free ortho-hydroxy cinnamates by Heck-Matsuda arylations: a scalable total synthesis of (R)-tolterodine.[Pubmed: 23190249]

Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.

Re: Cost-effectiveness of percutaneous tibial nerve stimulation versus extended release tolterodine for overactive bladder: H. W. Chen, R. S. Bercik, E. F. Werner And S. F. Thung; J Urol 2012; 187: 178-184.[Pubmed: 23088965]


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