260389-90-0

Basic information

• Product Name: (S)-2-(3-(diisopropylaMino)-1-phenylpropyl)-4-(hydroxyMethyl)phenol
• Synonyms: (S)-2-(3-(diisopropylaMino)-1-phenylpropyl)-4-(hydroxyMethyl)phenol;(S)-5-HydroxyMethyl Tolterodine
• CAS NO: 260389-90-0
• Molecular Formula: C₂₂H₃₁NO₂
• Molecular Weight: 341.48704
• Product Categories: Amines, Aromatics, Inhibitors, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 260389-90-0.mol

Chemical Properties

• Boiling Point: 490.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.060±0.06 g/cm3(Predicted)
• PKA: 9.61±0.48(Predicted)
• CAS DataBase Reference: (S)-2-(3-(diisopropylaMino)-1-phenylpropyl)-4-(hydroxyMethyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(3-(diisopropylaMino)-1-phenylpropyl)-4-(hydroxyMethyl)phenol(260389-90-0)
• EPA Substance Registry System: (S)-2-(3-(diisopropylaMino)-1-phenylpropyl)-4-(hydroxyMethyl)phenol(260389-90-0)

Safety Data

• Hazardous Substances Data: 260389-90-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
(S)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol is used as an active pharmaceutical ingredient for the treatment of specific medical conditions. Its unique structure may allow it to interact with biological targets, such as receptors or enzymes, in a way that provides therapeutic benefits.
Used in Chemical Synthesis:
In the chemical industry, (S)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol can be used as a building block or intermediate in the synthesis of more complex molecules. Its functional groups and chiral center may be exploited to create a variety of compounds with different properties and applications.
Used in Drug Metabolism Studies:
As a metabolite of a parent drug, (S)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol can be used in research to understand the metabolic pathways and pharmacokinetics of the parent compound. This information is crucial for drug development and optimization.
Used in Urinary Incontinence Treatment:
Drawing a parallel from the provided material on (S)-5-Hydroxymethyl Tolterodine, a metabolite of Tolterodine used for urinary incontinence, it is plausible that (S)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol could also be used as a therapeutic agent in the treatment of urinary incontinence or other related conditions, leveraging its interactions with muscarinic receptors.

Upstream product

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Relevant articles and documents

Bacterial Biosynthetic P450 Enzyme PikCD50N: A Potential Biocatalyst for the Preparation of Human Drug Metabolites

Human drug metabolites (HDMs) are important chemicals widely used in drug-related studies. However, acquiring these enzyme-derived and regio-/stereo-selectively modified compounds through chemical approaches is complicated. PikC is a biosynthetic P450 enz

Formal synthesis of fesoterodine by acid-facilitated aromatic alkylation

The competitive muscarinic receptor antagonist fesoterodine is a congener of tolterodine and has better efficiency compared to tolterodine. In this study, we present an efficient synthesis of the fesoterodine intermediate 3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzaldehyde from ethyl benzoylacetate by Friedel-Crafts alkylation in the presence of an acid as a key reaction step. The synthesis is carried out by the reduction of the ketoester to a 1,3-diol, diisopropylamine substitution, and Friedel-Crafts alkylation, followed by reduction and chiral resolution.

The lactol route to fesoterodine: An amine-promoted Friedel-Crafts alkylation on commercial scale

We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.