129784-12-9

Basic information

• Product Name: Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]-
• Synonyms: Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]-;Pyrrolidinium, 3-[[(2R)-cyclopentylhydroxyphenylacetyl]oxy]-1,1-dimethyl-, bromide, (3S)-
• CAS NO: 129784-12-9
• Molecular Formula: C19H28 N O3 . Br
• Molecular Weight: 0
• Mol File: 129784-12-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]-(129784-12-9)
• EPA Substance Registry System: Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]-(129784-12-9)

Safety Data

• Hazardous Substances Data: 129784-12-9(Hazardous Substances Data)

Usage

General Description

Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]- is a chemical compound that belongs to the family of pyrrolidinium salts. It is a bromide salt that contains a pyrrolidinium cation and a complex anion with a cyclopentylhydroxyphenylacetyl group. Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide, [S-(R*,S*)]- is chiral, with both S and R configurations present, and it is commonly used in pharmaceutical research and synthesis. It has potential applications in drug delivery systems, as well as in the development of new pharmaceutical compounds and formulations. Its specific properties and potential uses make it a subject of interest for researchers and scientists in the pharmaceutical industry.

Upstream product

• 74-83-9 methyl bromide 
• 13118-11-1 3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine 
• 13220-33-2 1-methyl-3-pyrrolidinol 
• 427-49-6 2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 25726-04-9 phenylglyoxylyl chloride 
• 611-73-4 Benzoylformic acid 
• 5763-56-4 2-Cyclopentyl-2-oxoacetic acid 
• 124-40-3 dimethyl amine 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 19833-96-6 2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester 
• 129784-12-9 (3R)-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide 

Downstream Products

• 129784-12-9 R,R-glycopyrrolate 
• 873295-46-6 (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate) 
• 873295-45-5 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium benzoate 

Relevant articles and documents

Discovery of Novel Potent Muscarinic M3 Receptor Antagonists with Proper Plasma Stability by Structural Recombination of Marketed M3 Antagonists

The marketed long-acting M3 antagonists for treatment of chronic obstructive pulmonary disease have inappropriate plasma stability (either overstable or excessively unstable), which causes substantial systemic exposure or poor patient compliance. To discover novel M3 antagonists with proper plasma stability, we synthesized and biologically evaluated a series of chiral quaternary ammonium salts of pyrrolidinol esters, which were designed by structural recombination of the marketed M3 antagonists. As a result, two novel potent M3 antagonists, (R/S)-3-[2-hydroxy-2,2-di(thiophen-2-yl)acetoxy]-1,1-dimethylpyrrolidinium bromides (1 a: Ki=0.16 nm, IC50=0.38 nm, t1/2=9.34 min; 1 b: Ki=0.32 nm, IC50=1.01 nm, t1/2=19.2 min) with proper plasma stability were identified, which (particularly 1 a) hold great promise as clinical drug candidates to overcome the drawbacks caused by the inappropriate stability of the currently marketed M3 antagonists. In addition, structure–activity relationship studies revealed that the R configuration of the pyrrolidinyl C3 atom was clearly better than the S configuration.

Synthesis process of glycopyrronium bromide

The invention discloses a synthesis process of a glycopyrronium bromide bulk drug, and the process comprises the following steps: carrying out hydroxyl protection on an a-cyclopentyl mandelic acid compound by using a dihydropyran compound, carrying out esterification reaction, removing a protecting group, and finally carrying out quaternization reaction to obtain glycopyrronium bromide. The method is mild in reaction condition, does not need to introduce a large amount of auxiliaries and solvents, conforms to the green chemistry principle, and is suitable for industrialization.

A preparation method of the glycopyrrolate

The invention discloses a method for preparation of glycopyrrolate, firstly the α - cyclopentyl mandelic acid for benzyl protected hydroxy, then the conventional method and 1 - methyl - 3 - pyrrolidinol esterification of key intermediate pyrrolidinol ester; in the middle of the invention supplies the key under the condition of Pd/C debenzylation, finally methyl bromide quaternary ammonium formation salting out the solid filter and get the glycopyrrolate crude, refined is obtained when the location of the qualified products. In order to prevent the occurrence of side reactions, the method of using very low cost introduced into hydroxyl protective agent benzyl, greatly improves the yield, simplifying the post-treatment, reduces the amount of waste water. The method of the invention with the production operation is simple, the production cost is low, raw materials are easy, high yield, low pollution and the like, the resulting product in accordance with the pharmaceutical quality standards.