2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

Base Information

• Chemical Name: 2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol
• CAS No.: 200801-70-3
• Molecular Formula: C22H31NO2
• Molecular Weight: 341.494
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80432981
• Nikkaji Number: J970.120F
• Mol file: 200801-70-3.mol

Synonyms:200801-70-3;2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol;rac 5-Hydroxymethyl Tolterodine;rac 5-Hydroxymethyl Tolterodine, 90% by HPLC;(Rac)-5-Hydroxymethyl Tolterodine;2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol;2-{3-[bis(propan-2-yl)amino]-1-phenylpropyl}-4-(hydroxymethyl)phenol;3-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol;2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol;2-{3-[Di(propan-2-yl)amino]-1-phenylpropyl}-4-(hydroxymethyl)phenol;3-(3-(Bis(1-methylethyl)amino)-1-phenylpropyl)-4-hydroxybenzenemethanol;SCHEMBL580657;rac-5-Hydroxymethyl Tolterodine;(Rac)-PNU-200577;DTXSID80432981;HMS3656F09;CS-M1035;AKOS022182757;Benzenemethanol, 3-[3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxy-;CS-O-10476;AS-73207;HY-76570;FT-0669853;FT-0669854;C11364;EN300-18702853;J-012995;Z2574924591;2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol;2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethylphenol;(+/-)-2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethylphenol;(+/-)-2-(3-Diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol;(+/-)-2-(3-Diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol;(+/-)-2-(3-diisopropylamino-1-phenyl propyl)-4-hydroxy methyl phenol

Chemical Property of 2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 52-53°C
• Boiling Point: 490.721oC at 760 mmHg
• PKA: 9.61±0.48(Predicted)
• Flash Point: 233.165oC
• PSA: 43.70000
• Density: 1.061g/cm3
• LogP: 4.52530
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (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:

98%,99%, ^*data from raw suppliers

rac-5-Hydroxymethyl Tolterodine, 90% by HPLC ^*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
• Uses: rac 5-Hydroxymethyl Tolterodine can be used as a metabolite of Tolterodine, a muscarinic receptor antagonist used in the treatment of urinary incontinence. A metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence. Also, a degradation product of Fesoterodine (F321300) formed under stress condit ions in tablet dosage forms. A metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence. Also, a degradation product of Fesoterodine (F321300) formed under stress conditions in tablet dosage forms.

Technology Process of 2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

There total 37 articles about 2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol 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: 92.0%

3-[3-(N,N-diisopropylamino)-1-phenylpropyl]-4-hydroxybenzaldehyde → RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine (200801-70-3)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In ethanol; at -10 - 20 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1002/bkcs.10592

Reference yield: 89.0%

(2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl)methanol (959624-24-9) + diisopropylamine (108-18-9) → RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine (200801-70-3)

Guidance literature:

(2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl)methanol; diisopropylamine; In methanol; at 40 ℃; for 1.25h;

With hydrogen; 5%-palladium/activated carbon; In methanol; at 40 ℃; for 20h; under 5947.36 Torr;

Reference yield: 65.1%

N,N-diisopropyl-3-(2-hydroxy-5-methyloxycarbonylphenyl)-3-phenylpropanamine (214601-16-8) → RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine (200801-70-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 0 - 30 ℃; Inert atmosphere;

upstream raw materials:

(2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl)methanol

diisopropylamine

(-)-N,N-diisopropyl-3-(2-benzyloxy-5-hydroxymethylphenyl)-3-phenylpropylamine

N,N-diisopropyl-3-(2-hydroxy-5-methyloxycarbonylphenyl)-3-phenylpropanamine

Downstream raw materials:

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

fesoterodine

PNU 200577 l-mandelate salt

fesoterodine fumarate

Refernces

• 1、 -. "Synthetic Method of Intermediate for Fesoterodine". Paragraph 0068; 0069. . Retrieved 2017/12/01.
• 2、 -. "PROCESS FOR THE PREPARATION OF 2-HYDROXY-4-PHENYL-3,4-DIHYDRO-2H-CHROMEN-6-YL-METHANOL AND (R)-FESO-DEACYL". Paragraph 0076; 0077. . Retrieved 2013/04/10.