136310-66-2

Basic information

• Product Name: rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate
• Synonyms: rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate;Tiotropium EP Impurity D
• CAS NO: 136310-66-2
• Molecular Formula: C₁₈H₁₉NO₃S₂
• Molecular Weight: 361.47836
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 136310-66-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 522.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 10.33±0.29(Predicted)
• CAS DataBase Reference: rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate(136310-66-2)
• EPA Substance Registry System: rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate(136310-66-2)

Safety Data

• Hazardous Substances Data: 136310-66-2(Hazardous Substances Data)

Usage

Uses

(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-ylacetate is an impurity in the synthesis of Tiotropium Bromide (T444850), a muscarinic receptor antagonist. Bronchodilator.

Upstream product

• 26447-85-8 hydroxy-di-thiophen-2-yl-acetic acid methyl ester 
• 20513-09-1 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol 
• 22143-95-9 tropenol 
• 672-21-9 (+/-)-Scopolamine hydrobromide 
• 22150-33-0 (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester 

Downstream Products

• 139404-48-1 tiotropium bromide 
• 136310-64-0 N-demethyltiotropium 

Relevant articles and documents

Preparation method of tiotropium bromide

The invention provides a preparation method of tiotropium bromide, which comprises the following steps: (1) reacting a compound of a formula I with a compound of a formula II with an alkaline compound to obtain a compound of a formula III, wherein R is methyl, ethyl, isopropyl or tert-butyl, (2) reacting a halogenating agent of the compound of the formula III with a catalyst to obtain a compound of a formula IV, reacting the compound of the formula IV with an alkali to obtain a compound V, wherein X is Cl, Br or I, and (3) reacting the compound of the formula V with methyl bromide to obtain the tiotropium bromide. According to the method, the defect that vanadium pentoxide and hydrogen peroxide-urea are used as epoxidation agents when tropine is used as a raw material to prepare tiotropium bromide in the prior art is overcome, the reaction safety is improved, and meanwhile, the yield of cyclized products is increased.

Synthesis and radiolabelling of ipratropium and tiotropium for use as PET ligands in the study of inhaled drug deposition

Ipratropium bromide [(1R,3r,5S,8r,2′RS)-3-(3′-hydroxy-2′- phenylpropionyloxy)-8-isopropyl-8-methyl-8-aza-bicyclo[3.2.1]octan-8-ium bromide] and tiotropium bromide [(1R,2R,4S,5S,7s)-7-[2′-hydroxy-2′, 2′-di(thiophen2″-yl)acetoxy]-9,9-dimethyl-9-aza-3-oxatricyclo[3.3.1. 02,4]nonan-9-ium bromide] are inhaled drugs used in the treatment of chronic obstructive pulmonary disease (COPD) and asthma. Tertiary amine precursors have been synthesized and radiolabelled with carbon-11 by N-alkylation with [11C]CH3I. The [11C] ipratropium and [11C]tiotropium positron emission tomography (PET) ligands are obtained with high radiochemical purity, in 0.3 and 0.5% non-decay corrected yields based on [11C]CO2 at end-of-synthesis and specific activities of 11 and 18 GBq μ mol-1, respectively, calculated at end-of-synthesis. These PET radioligands can be used in the study of inhaled drug deposition. CSIRO 2006.