135271-47-5

Basic information

• Product Name: R-(-)-Salmeterol
• Synonyms: (R)-Salmeterol;1,3-Benzenedimethanol, 4-hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-, (a1R)- (9CI);1,3-Benzenedimethanol, 4-hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-, (R)-;R-(-)-Salmeterol;(R)-1-[3-(Hydroxymethyl)-4-hydroxyphenyl]-2-[[6-(4-phenylbutoxy)hexyl]amino]ethanol;(R)-4-Hydroxy-3-hydroxymethyl-α-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]benzenemethanol;2-(Hydroxymethyl)-4-[(R)-1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenol;2-(Hydroxymethyl)-4-[(R)-2-[[6-(4-phenylbutoxy)hexyl]amino]-1-hydroxyethyl]phenol
• CAS NO: 135271-47-5
• Molecular Formula: C25H37NO4
• Molecular Weight: 415.57
• Mol File: 135271-47-5.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: R-(-)-Salmeterol(CAS DataBase Reference)
• NIST Chemistry Reference: R-(-)-Salmeterol(135271-47-5)
• EPA Substance Registry System: R-(-)-Salmeterol(135271-47-5)

Safety Data

• Hazardous Substances Data: 135271-47-5(Hazardous Substances Data)

Usage

Description

R-(-)-Salmeterol is a bronchodilator and a long-acting beta-agonist (LABA) that is used to treat asthma and chronic obstructive pulmonary disease (COPD). It works by relaxing the muscles in the airways, allowing the lungs to expand and making it easier to breathe.
Used in Pharmaceutical Industry:
R-(-)-Salmeterol is used as a bronchodilator for treating asthma and chronic obstructive pulmonary disease (COPD). It helps in relaxing the muscles in the airways, allowing the lungs to expand and making it easier to breathe. This medication is typically inhaled through a special device and should be used regularly as prescribed by a healthcare professional to help control and prevent symptoms of asthma and COPD.

Upstream product

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• 163923-18-0 N-[6-(4-phenylbutoxy)hexyl] benzenemethanamine hydrochloride 
• 1351281-52-1 methyl 5-(2-(benzyl(6-(4-phenylbutoxy)hexyl)amino)acetyl)-2-(benzyloxy)benzoate 
• 943969-38-8 2-(benzyl-(6-(4-phenylbutoxy)hexyl)amino)-1-(4-(benzyloxy)-3-(hydroxymethyl)phenyl)ethanol 
• 89365-50-4 salmeterol 
• 94749-73-2 6-bromohexyl 4-phenylbutyl ether 
• 54030-33-0 2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-carboxaldehyde 

Relevant articles and documents

Enantioselective synthesis of (R)-salmeterol employing an asymmetric Henry reaction as the key step

A practical synthesis of (R)-salmeterol has been accomplished from 3-bromo salicylaldehyde, which involved a Cu(II)-sparteine complex catalyzed asymmetric Henry reaction as the key step. (R)-Salmeterol can be obtained in 39% overall yield and 95% ee.

Structural isomers of saligenin-based β2-agonists: Synthesis and insight into the reaction mechanism

Salmeterol and albuterol are well-known β2-adenoreceptor agonists widely used in the treatment of inflammatory respiratory diseases, such as bronchial asthma and chronic obstructive pulmonary disease. Here we report the preparation of structural isomers of salmeterol and albuterol, which can be obtained from the same starting material as the corresponding β2-agonists, depending on the synthetic approach employed. Using 1D and various 2D NMR measurements, we determined that the structure of prepared isomers holds the β-aryl-β-aminoethanol moiety, in contrast to the α-aryl-β-aminoethanol moiety found in salmeterol and albuterol. We investigated the reaction of β-halohydrin and amines responsible for the formation of β-aryl-β-amino alcohol-both experimentally and using computational methods. The structure of β-halohydrin with the methyl salicylate moiety imposes the course of the reaction. The solvent plays a relevant, yet ambiguous role in the direction of the reaction, while the strength of the base influences the reaction yield and isomer ratio in a more evident way. Using computational methods, we have shown that the most probable reaction intermediate responsible for the formation of the unexpected isomer is the corresponding para-quinone methide, which can be formed due to phenol present in the methyl salicylate moiety. After successful preparation of albuterol and salmeterol isomers, we tested their inhibition potency to human acetylcholinesterase (AChE) and usual and atypical butyrylcholinesterase (BChE). Kinetic studies revealed that both isomers are low-potency reversible inhibitors of human cholinesterases.

Preparation method of salmeterol base

The invention discloses a preparation method of salmeterol. The method includes the following steps: carrying out a condensation reaction on a compound 2 and a compound 3 under an alkaline condition to obtain an intermediate 4; carrying out acidic hydrolysis to obtain an intermediate 5, and reducing the intermediate 5 to obtain an intermediate 6; and removing a benzyl group from the intermediate 6 by using palladium on carbon (Pd/C) to obtain a salmeterol base. The preparation method has the advantages of mild reaction conditions, simple post-treatment, low cost, high yield high product purity, and easiness in realization of industrialization.

PROCESS FOR THE PREPARATION OF SALMETEROL XINAFOATE

The present invention relates to an improved process for the preparation of Salmeterol Xinafoate of Formula (I).