959624-24-9

Usage

Uses

Used in Pharmaceutical Industry:
6-(hydroxyMethyl)-4-phenylchroMan-2-ol is used as a potential pharmaceutical agent due to its unique structure and possible biological activity. Its specific functional groups and molecular configuration may contribute to its efficacy in treating certain conditions or diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-(hydroxyMethyl)-4-phenylchroMan-2-ol is utilized as a compound with potential therapeutic properties. Its intricate structure allows for exploration in drug design and development, possibly leading to new medications or therapies.
Used in Scientific Research:
6-(hydroxyMethyl)-4-phenylchroMan-2-ol serves as a subject of interest in scientific research, where its properties and potential uses are investigated. This can lead to a better understanding of its behavior in various chemical reactions and its interactions with biological systems.

Upstream product

• 126070-20-0 4-((tert-butyldimethylsilyloxy)methyl)phenol 
• 117635-46-8 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene 
• 18401-58-6 4-(trimethylsilyloxymethyl)phenoxytrimethylsilane 
• 14371-10-9 (E)-3-phenylpropenal 
• 115255-87-3 4-trimethylsilyloxymethylphenol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 959624-43-2 [2-(4-methylpiperazin-1-yl)-4-phenyl-chroman-6-yl]-methanol 

Downstream Products

• 200801-70-3 RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine 
• 286930-02-7 fesoterodine 
• 1312416-97-9 C₁₆H₁₈O₃ 
• 286930-03-8 fesoterodine fumarate 
• 207679-81-0 (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol 
• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 1333234-72-2 (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol (R)-2-acetoxy(phenyl)acetate 
• 260389-90-0 5-hydroxymethyl tolterodine 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF 2-HYDROXY-4-PHENYL-3,4-DIHYDRO-2H-CHROMEN-6-YL-METHANOL AND (R)-FESO-DEACYL

The present invention regards an improved and industrially advantageous process for the preparation of the 2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl-methanol intermediates, also called “feso chromenyl” and (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol, also called “(R)-feso deacyl”, which are in turn used in the synthesis of fesoterodine and in particular of fesoterodine fumarate. This process utilises reagents which are non-toxic and manageable at industrial level and enables obtaining a new stable and non-hygroscopic crystalline form of the key intermediate “(R)-feso deacyl”, called form B.

PROCESS FOR THE PREPARATION OF 2 -HYDROXY- 4 -PHENYL -3, 4 -DIHYDRO-2H-CHROMEN- 6 -YL -METHANOL AND (R) - FESO - DEACYL

The present invention regards an improved and industrially advantageous process for the preparation of the 2-hyaroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl-methanol intermediates, also called "feso chromenyl" and (R)-2-[3-(diisopropylamino)-l- phenylpropyl]-4-(hydroxymethyl)phenol, also called "(R)-feso deacyl", which are in turn used in the synthesis of fesoterodine and in particular of fesoterodine furnarate. This process utilises reagents which are non-toxic and manageable at industrial level and enables obtaining a new stable and non-hygroscopic crystalline form of the key intermediate "(R)-feso deacyl", called form B.

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.

PROCESS FOR THE PRODUCTION OF BENZOPYRAN-2-OL DERIVATIVES

The invention provides a process for the production of a compound of formula (I), wherein Y is selected from CH3, CH2OH, CH2CH2OH, CH2Br and Br; comprising the steps of: (i) reacting a compound of formula (II), wherein OX is hydroxy or O- M+, in which M+ is a cation selected from Li+, Na+ and K+, and Y is as defined above; with trans-cinnamaldehyde (III), in the presence of a secondary amine compound; then (ii) treating the product of the preceding step with acid to afford the compound of formula (I). The above process may be used in the production of tolterodine and fesoterodine, which are useful in the treatment of overactive bladder.