Tolterodine tartrate

Base Information

• Chemical Name: Tolterodine tartrate
• CAS No.: 209747-05-7
• Molecular Formula: C26H37NO7
• Molecular Weight: 475.57448
• European Community (EC) Number: 620-503-4
• UNII: 5T619TQR3R
• DSSTox Substance ID: DTXSID80924972
• Wikidata: Q27114836
• NCI Thesaurus Code: C29504
• RXCUI: 221174
• ChEMBL ID: CHEMBL1200871
• Mol file: 209747-05-7.mol

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

Chemical Property of Tolterodine tartrate

Chemical Property:

• Boiling Point: 442.2 °C at 760 mmHg
• Flash Point: 192.1 °C
• PSA: 138.53000
• LogP: 3.21880
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 475.25700252
• Heavy Atom Count: 34
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

Tolterodine L-tartrate 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)O)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(C(C(=O)O)O)(C(=O)O)O
• Isomeric SMILES: CC1=CC(=C(C=C1)O)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• 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.

Technology Process of Tolterodine tartrate

There total 58 articles about Tolterodine tartrate 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: 88.0%

N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride; With sodium carbonate; sodium hydroxide; In dichloromethane; water; at 20 ℃; for 1h;

L-Tartaric acid; In methanol; acetone; for 1h; Reflux;

DOI:10.1021/op7001134

Reference yield: 39.0%

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide (837376-36-0) + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide; With sodium hydroxide; In dichloromethane; water;

L-Tartaric acid; In ethanol; at 60 - 85 ℃;

Reference yield: 37.0%

(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide (897314-72-6) + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide; With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 5 - 40 ℃; for 6h; Cooling with ice;

L-Tartaric acid; In ethanol; at 0 - 70 ℃; Reflux;

upstream raw materials:

L-Tartaric acid

N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide

N,N-Diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropylamine

Downstream raw materials:

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

(R)-5-hydroxymethyl tolterodine fumarate salt

Refernces

• 1、 Korenaga, Toshinobu,Sasaki, Ryo,Takemoto, Toshihide,Yasuda, Toshihisa,Watanabe, Masahito. "Computationally-Led Ligand Modification using Interplay between Theory and Experiments: Highly Active Chiral Rhodium Catalyst Controlled by Electronic Effects and CH–π Interactions". supporting information. p. 322 - 333. Retrieved 2018/01/22.
• 2、 -. "Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate". Page/Page column 11. . Retrieved 2012/07/28.