1233378-72-7

Usage

Uses

Used in Organic Synthesis:
[3-[(1R)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate is used as a reagent in organic synthesis for its stability and mild reaction conditions. It facilitates the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, [3-[(1R)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate is used as a key component in the synthesis of various drugs. Its unique structure allows for the creation of novel pharmaceuticals with potential therapeutic applications.
Used in Prodrug Preparation:
[3-[(1R)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate is also utilized in the preparation of prodrugs, which are biologically inactive compounds that can be converted into active pharmaceuticals within the body. This application enhances the drug's bioavailability and allows for targeted drug delivery, improving the overall efficacy and safety of the treatment.

Upstream product

• 194545-44-3 (R)‐(+)‐3‐(1‐hydroxyethyl)phenol 
• 7143-01-3 Methanesulfonic anhydride 
• 121-71-1 3-Hydroxyacetophenone 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1233378-78-3 [(S)-3-(1-dimethylaminoethyl)phenyl] methanesulfonate 
• 139306-10-8 (S)-3-(1-dimethylaminoethyl)phenol 
• 123441-03-2 rivastigmin 

Relevant academic research and scientific papers

Rivastigmine method for the preparation of intermediates

The invention relates to the field of pharmaceutical synthesis, and particularly relates to a method for preparing a rivastigmine intermediate. The method employs hydroxy acetophenone as a raw material to prepare a rivastigmine chiral intermediate compound (R)-3-(1-hydroxyethyl) phenol under the action of a chiral catalyst, alkali and hydrogen. The chiral catalyst is a compound with the following structure; X represents H, C1-C8 alkyl, C1-C8 alkoxy, phenyl, substituted phenyl, 1-naphthyl, 2-naphthyl, ceteroary or benzyl; the phenyl substituent is C1-C8 alkyl and alkoxy, and in the number of 1-5; and the ceteroary is furan, thiophene or pyridine. The method for preparing the rivastigmine intermediate provided by the invention applies the chiral catalyst to obtain the rivastigmine intermediate (R)-3-(1-hydroxyethyl) phenol with high purity, and the intermediate has ee value greater than 97% through chiral HPLC analysis. The molar ratio of the catalyst only accounts for 1 / 100000-1 / 1000000 of reactant to achieve the required optical purity, and completely convert the reactant, thereby greatly saving the cost, increasing the yield and saving raw materials.

Industrial scale-up of enantioselective hydrogenation for the asymmetric synthesis of rivastigmine

Two efficient processes for the synthesis of rivastigmine, one of the most potent drugs for the treatment of mild-to-moderate dementia of the type presenting in Alzheimer's disease, has been developed. Of particular note is the processes used for the asymmetric hydrogenation by applying the highly efficient chiral spiro catalyst, Ir-SpiroPAP. The first route was easy to scale up in industry and provided the commercial intermediate (S)-3-(1- dimethylaminoethyl)phenol, 6, which is suitable for the manufacture of rivastigmine in active pharmaceutical ingredient (API) demand. The second route was convenient for operation and purification and completed the synthesis of rivastigmine (1) in four steps and 84% overall yield.

PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE COMPOUNDS USING PRESSURE HYDROGENATION

A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and pressure hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.

Process for the preparation of optically active compounds using transfer hydrogenation

A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.