35130-97-3

Basic information

• Product Name: Tropine-3-mesylate
• Synonyms: Tropine-3-mesylate;(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) methanesulfonate;8-Azabicyclo(3.2.1)octan-3-ol, 8-methylmethanesulfonate (ester), endo-;endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl Methanesulfonate;8-Azabicyclo[3.2.1]octan-3-ol,8-Methyl-, Methanesulfonate (1:1), (3-endo)-
• CAS NO: 35130-97-3
• Molecular Formula: C₉H₁₇NO₃S
• Molecular Weight: 219.3
• Mol File: 35130-97-3.mol

Chemical Properties

• Boiling Point: 347.1°Cat760mmHg
• Flash Point: 163.7°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 5.5E-05mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: Tropine-3-mesylate(CAS DataBase Reference)
• NIST Chemistry Reference: Tropine-3-mesylate(35130-97-3)
• EPA Substance Registry System: Tropine-3-mesylate(35130-97-3)

Safety Data

• Hazardous Substances Data: 35130-97-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tropine-3-mesylate is used as a reagent in organic synthesis for the creation of various pharmaceuticals and bioactive compounds due to its unique chemical properties and reactivity.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Tropine-3-mesylate is utilized as a key intermediate in the synthesis of drugs, contributing to the development of new therapeutic agents.
Used as a Cholinergic Antagonist:
Tropine-3-mesylate is used as a cholinergic antagonist to block the action of acetylcholine in the nervous system, which has potential applications in treating conditions affected by this neurotransmitter.
Used in Pharmaceutical Development for Asthma:
Tropine-3-mesylate is being studied for its potential therapeutic use in asthma treatment, where its cholinergic antagonist properties could provide relief from symptoms.
Used in Pharmaceutical Development for Motion Sickness:
In the context of motion sickness, Tropine-3-mesylate is explored for its potential to alleviate the discomfort associated with this condition, possibly through its effects on neurotransmitter activity.
Used in Pharmaceutical Development for Gastrointestinal Disorders:
For gastrointestinal disorders, Tropine-3-mesylate is considered for its potential therapeutic applications, possibly due to its influence on the nervous system and its interaction with acetylcholine.

InChI:InChI=1/C9H17NO3S/c1-10-7-3-4-8(10)6-9(5-7)13-14(2,11)12/h7-9H,3-6H2,1-2H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 120-29-6 3-tropanol 

Downstream Products

• 5911-81-9 3α-cyanotropane 
• 101353-61-1 3-endo-benzylamino-8-methyl-8-azabicyclo[3.2.1]octane 
• 569339-59-9 thioacetic acid S-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl) ester 
• 116568-67-3 tropane-3-carboxamide 
• 77863-05-9 3α-benzoyltropane 
• 107330-52-9 1-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-1,1-diphenylmethanol 
• 87571-88-8 3-endo-tropanamine 
• 5911-45-5 tropane-3exo-carbonitrile 
• 5911-34-2 tropane-3exo-carboxylic acid methyl ester 
• 1182358-02-6 (Exo)-3-(4-methoxybenzylsulfanyl)-8-methyl-8-azabicyclo[3.2.1]octane 
• 1433607-18-1 (E)-2-amino-7-(4-fluoro-2-(pyridin-3-yl)phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-((1S,3R,5R)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)oxime 
• 224452-66-8 retapamulin 
• 848130-83-6 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-thiol 

Relevant articles and documents

A Swedish he Moline synthesis method

The present invention provides a synthesis method for Retapamulin. The method comprises: using pleuromutilin as a starting material of one segment; obtaining PLM-TS by condensation reaction between the starting material and toluenesulfonyl chloride; using tropenol as a raw material of the other segment; obtaining TRP-MS by reaction between the raw material and toluenesulfonyl chloride; after performing substitution reaction between TRP-MS that uses water as a solvent and potassium ethyl xanthate, performing acidification between the substance and sulfuric acid to obtain an intermediate TRP-XAN; TRP-XAN undergoing hydrolysis in an ethanol NaOH solution; performing acidification between the substance and sulfuric acid to obtain an intermediate TRP-THI; the two segments TRP-THI and PLM-TS undergoing condensation reaction under alkaline conditions to obtain the final product, Retapamulin. The synthesis method for Retapamulin provided by the present invention is simple, environmentally friendly, easy in controlling the quality of intermediates of all steps, and suitable for the Retapamulin synthesis process in industrialized production.

Process for the preparation of Retapamulin and its intermediates

Processes for preparing tropine derivatives of the following Formula B are provided where LG represents a leaving group. The tropine derivatives may be used to prepare Retapamulin, preferably in substantially pure form. Also provided are processes for preparing Retapamulin comprising combining a base, tropine thiol in a free base or salt form, an organic solvent, and a pleuromutilin derivative of Formula A:

A convenient microwave-assisted arylstannane generation-Stille coupling protocol

An efficient methodology for the synthesis of complex pyridin-3-yl-phenyl biaryl systems is described; microwave irradiation greatly enhances the rate of the two Pd-catalyzed key steps: formation of the stannane partner and its subsequent Stille coupling with a range of highly functionalized pyridines. Besides being fast and high yielding, this process also allows diversification of the pyridine at a late stage.