Desfesoterodine

Base Information

• Chemical Name: Desfesoterodine
• CAS No.: 207679-81-0
• Molecular Formula: C22H31NO2
• Molecular Weight: 341.494
• Hs Code.: 2922509090
• European Community (EC) Number: 929-946-0,801-894-2
• UNII: YU871O78GR
• DSSTox Substance ID: DTXSID40431319
• Nikkaji Number: J817.122J
• Wikipedia: Desfesoterodine
• Wikidata: Q27294711
• NCI Thesaurus Code: C169886
• Metabolomics Workbench ID: 155549
• ChEMBL ID: CHEMBL3348932
• Mol file: 207679-81-0.mol

Synonyms:(R)-N,N-diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropanamine;5-hydroxymethyl tolterodine;PNU 200577;PNU-200577

Chemical Property of Desfesoterodine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 68-72 °C
• Refractive Index: 1.563
• Boiling Point: 490.721 °C at 760 mmHg
• PKA: 9.61±0.48(Predicted)
• Flash Point: 233.165 °C
• PSA: 43.70000
• Density: 1.061 g/cm³
• LogP: 4.52530
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 341.235479232
• Heavy Atom Count: 25
• Complexity: 357

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-5-HydroxymethylTolterodine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(CCC(C1=CC=CC=C1)C2=C(C=CC(=C2)CO)O)C(C)C
• Isomeric SMILES: CC(C)N(CC[C@H](C1=CC=CC=C1)C2=C(C=CC(=C2)CO)O)C(C)C
• Uses: (R)-5-HydroxyMethyl Tolterodine is a metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence. A metabolite of Tolterodine, a muscarinic receptor antagonist used in the treatment of urinary incontinence.

Technology Process of Desfesoterodine

There total 103 articles about Desfesoterodine 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: 98.0%

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester (214601-16-8) → (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0)

Guidance literature:

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester; With sodium hydroxide; In methanol; at 0 - 35 ℃; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 5 - 25 ℃; for 4h;

With water; sodium hydroxide; In tetrahydrofuran; at 0 - 5 ℃; for 3h;

Reference yield: 98.0%

{4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]phenyl}methanol (156755-37-2) → (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0)

Guidance literature:

With hydrogen; 5% Pd(II)/C(eggshell); In methanol; at 50 - 55 ℃;

Reference yield: 95.0%

methyl (R)-(-)-3-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoate 2,3-dibenzoyl-D-tartaric acid salt (1294517-15-9) → (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0)

Guidance literature:

methyl (R)-(-)-3-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoate 2,3-dibenzoyl-D-tartaric acid salt; With sodium hydrogencarbonate; In ethyl acetate; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 3.5h;

With ammonium chloride; In tetrahydrofuran; at -10 - 20 ℃; for 0.5h;

upstream raw materials:

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

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

diisopropylamine

(R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine

Downstream raw materials:

(R)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol formate

fesoterodine fumarate

PNU 200577 l-mandelate salt

lithium (R)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol

Refernces

• 1、 -. "NOVEL (R) AND RAC 3-(2-(ALLYLOXY)-5-METHYLPHENYL)-N,N-DIISOPROPYL-3- PHENYLPROPAN-1-AMINE AND ITS USE FOR SYNTHESIS OF (R) AND RAC-2-(3- (DIISOPROPYLAMINO)-1-PHENYLPROPYL)-4-(HYDROXYMETHYL)PHENOL". Page/Page column 24; 25. . Retrieved 2017/09/05.
• 2、 -. "PROCESS FOR THE PREPARATION OF OPTICALLY PURE FESOTERODINE DERIVATIVES". Paragraph 0243; 0244. . Retrieved 2015/04/15.