13118-11-1

Basic information

• Product Name: 1-methylpyrrolidin-3-yl cyclopentylphenylglycolate
• Synonyms: 1-methylpyrrolidin-3-yl cyclopentylphenylglycolate;N-Methyl-3-pyrrolidinyl Cyclopentylmandelate;α-Cyclopentyl-mandelic Acid 1-Methyl-3-pyrrolidinyl Ester;α-Cyclopentyl-α-hydroxy-benzeneacetic Acid 1-Methyl-3-pyrrolidinyl Ester;a-Cyclopentyl-a-hydroxy-benzeneacetic Acid 1-Methyl-3-pyrrolidinyl Ester;a-Cyclopentyl-mandelic Acid 1-Methyl-3-pyrrolidinyl Ester;α-Cyclopentyl-α-hydroxybenzeneacetic acid 1-methylpyrrolidin-3-yl ester;Glycopyrrolate Related Compound B (75 mg) (1-Methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate)
• CAS NO: 13118-11-1
• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.396
• EINECS: 236-047-0
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles
• Mol File: 13118-11-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 434.6°Cat760mmHg
• Flash Point: 216.7°C
• Appearance: /
• Density: 1.17±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.5256 (589.3 nm 23℃)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.19±0.29(Predicted)
• CAS DataBase Reference: 1-methylpyrrolidin-3-yl cyclopentylphenylglycolate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylpyrrolidin-3-yl cyclopentylphenylglycolate(13118-11-1)
• EPA Substance Registry System: 1-methylpyrrolidin-3-yl cyclopentylphenylglycolate(13118-11-1)

Safety Data

• Hazardous Substances Data: 13118-11-1(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Oil

Uses

Glycopyrrolate impurity.

InChI:InChI=1/C18H25NO3/c1-19-12-11-16(13-19)22-17(20)18(21,15-9-5-6-10-15)14-7-3-2-4-8-14/h2-4,7-8,15-16,21H,5-6,9-13H2,1H3

Upstream product

• 13220-33-2 1-methyl-3-pyrrolidinol 
• 19833-96-6 2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester 
• 427-49-6 2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 108-86-1 bromobenzene 
• 137-43-9 Cyclopentyl bromide 
• 25726-04-9 phenylglyoxylyl chloride 
• 611-73-4 Benzoylformic acid 
• 5763-56-4 2-Cyclopentyl-2-oxoacetic acid 
• 91832-73-4 1-methylpyrrolidin-3-yl methanesulfonate 
• 60499-30-1 toluene-4-sulfonic acid 1-methylpyrrolidin-3-yl ester 

Downstream Products

• 129784-12-9 (3RS)-3-[(2SR)-(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1, 1-dimethylpyrrolidinium bromide 
• 129784-12-9 (3RS,2'RS)-3-[(cyclopentyl-hydroxyphenylacetyl)-oxy]-1,1-dimethylpyrrolidinium bromide 
• 873295-31-9 [(cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium chloride 
• 873295-31-9 [(cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium chloride 
• 65976-16-1 1-benzyl-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1-methylpyrrolidinium bromide 
• 129784-12-9 (3R,2'S)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide 
• 129784-12-9 (3S,2'R)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide 
• 596-51-0 glycopyrronium bromide 

Relevant articles and documents

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.

PROCESS FOR PREPARATION OF GLYCOPYRROLATE INTERMEDIATE

The present invention discloses an improved process for preparation of highly pure cyclopentyl mandelic acid derivative of formula (I), an intermediate of glycopyrrolate, without using hazardous chemicals.

PROCESS FOR SYNTHESIS OF GLYCOPYRRONIUM BROMIDE

Provided herein are processes for preparation of glycopyrronium bromide comprising reaction of N-methylpyrrolidin-3-ol with compounds of Formula I or Formula II followed by additional steps.