Tolterodine

Base Information

• Chemical Name: Tolterodine
• CAS No.: 124937-51-5
• Deprecated CAS: 215929-30-9
• Molecular Formula: C22H31NO
• Molecular Weight: 325.494
• European Community (EC) Number: 805-304-4
• UNII: WHE7A56U7K
• DSSTox Substance ID: DTXSID3023687
• Nikkaji Number: J561.859B
• Wikipedia: Tolterodine
• Wikidata: Q424312
• NCI Thesaurus Code: C62083
• RXCUI: 119565
• Pharos Ligand ID: 39LQRXW2W8BV
• Metabolomics Workbench ID: 43278
• ChEMBL ID: CHEMBL1382
• Mol file: 124937-51-5.mol

Synonyms:Detrol;Detrol LA;Detrusitol;PHA 686464B;PHA-686464B;PHA686464B;Tartrate, Tolterodine;tolterodine;tolterodine tartrate;Unidet;Urotrol

Chemical Property of Tolterodine

Chemical Property:

• Appearance/Colour: white like or light brown crystalline powder
• Vapor Pressure: 2.02E-09mmHg at 25°C
• Boiling Point: 442.2 °C at 760 mmHg
• PKA: pKa 9.8 (Uncertain)
• Flash Point: 192.1 °C
• PSA: 23.47000
• Density: 1.003 g/cm³
• LogP: 5.34140
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 325.240564612
• Heavy Atom Count: 24
• Complexity: 340

Purity/Quality:

98% ^*data from raw suppliers

R-(+)-Tolterodine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 63-51/53
• Safety Statements: 22-36/37-57

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticholinergic Agents
• Canonical SMILES: CC1=CC(=C(C=C1)O)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2
• Isomeric SMILES: CC1=CC(=C(C=C1)O)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2
• Recent ClinicalTrials: Tolterodine Relieves Overactive Bladder Symptoms in Women With Moderate-to-severe Obstructive Sleep Apnea Syndrome
• Recent EU Clinical Trials: An International Phase 3, Randomized, Double-Blind, Active (Tolterodine)-Controlled Multicenter Extension Study to Evaluate the Long-Term Safety and Efficacy of Vibegron in Patients with Symptoms of Overactive Bladder
• Recent NIPH Clinical Trials: A randomized controlled trial for beta agonist on ulolithiasis patients associated with overactive bladder.
• Uses: A muscarinic receptor antagonist. Used in the treatment of urinary incontinence.
• Therapeutic Function: Anticholinergic

Technology Process of Tolterodine

There total 65 articles about Tolterodine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (848768-06-9) → (R)-(+)-tolterodine (124937-51-5,124937-53-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 24h;

DOI:10.1021/ol702879u

Reference yield: 98.0%

(R)-N,N-diisopropyl-3-[2-(benzyloxy)-5-methylphenyl]-3-phenylpropan-1-amine → (R)-(+)-tolterodine (124937-51-5,124937-53-7)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; at 50 ℃; for 22h;

DOI:10.1021/ol702879u

Reference yield: 93.0%

(4R)-6-methyl-4-phenylchroman-2-ol (828933-86-4) + diisopropylamine (108-18-9) → (R)-(+)-tolterodine (124937-51-5,124937-53-7)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/ol9020404

upstream raw materials:

(R)-3-(2-Benzyloxy-5-methyl-phenyl)-N,N-diisopropyl-3-phenyl-propionamide

(R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

(4R)-6-methyl-4-phenylchroman-2-ol

diisopropylamine

Downstream raw materials:

(R)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

{4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]phenyl}methanol

(R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

(R)-5-hydroxymethyl tolterodine fumarate salt

Refernces

• 1、 Fujihara, Rina,Nakata, Kenya. "Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3". . p. 6566 - 6573. Retrieved 2018.
• 2、 Tian, Duanshuai,Xu, Ronghua,Zhu, Jinbin,Huang, Jianxun,Dong, Wei,Claverie, Jerome,Tang, Wenjun. "Asymmetric Hydroesterification of Diarylmethyl Carbinols". supporting information. p. 6305 - 6309. Retrieved 2021/02/09.
• 3、 Zullo, Valerio,Iuliano, Anna. "Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 3-Arylpropenoates: Enantioselective Synthesis of (R)-Tolterodine". . p. 1377 - 1384. Retrieved 2019/01/04.