Scopine-2,2-dithienyl glycolate

Base Information

• Chemical Name: Scopine-2,2-dithienyl glycolate
• CAS No.: 136310-64-0
• Molecular Formula: C18H19NO4S2
• Molecular Weight: 377.485
• Mol file: 136310-64-0.mol

Synonyms:2-Thiopheneaceticacid, a-hydroxy-a-2-thienyl-,9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (1a,2b,4b,5a,7b)-;3-Oxa-9-azatricyclo[3.3.1.02,4]nonane,2-thiopheneacetic acid deriv.;Di(2-thienyl)glycolic acid scopine ester;N-Demethyl tiotropium;Scopinedi(2-thienylglycolate);Scopine hydroxydi(2-thienyl)acetate;

Chemical Property of Scopine-2,2-dithienyl glycolate

Chemical Property:

• Vapor Pressure: 1.37E-12mmHg at 25°C
• Melting Point: 138-140°C
• Refractive Index: 1.687
• Boiling Point: 542.3 ºC at 760 mmHg
• PKA: 10.32±0.29(Predicted)
• Flash Point: 281.7 ºC
• PSA: 118.78000
• Density: 1.48 g/cm³
• LogP: 2.13900
• Storage Temp.: -20°C Freezer

Purity/Quality:

99% Min, ^*data from raw suppliers

ScopineDi(2-thienylglycolate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Scopine-2,2-dithienyl glycolate is an organic compound.?It is off-white solid. The melting point is 138-140°C. The storage temperature is -20°C. Scopine-2,2-dithienyl glycolate is one of the reaction intermediates in the preparation of tiotropium bromide, which is a highly effective anticholinergic agent and widely used for treatment of asthma and/or chronic obstructive pulmonary disease (COPD) (chronic obstructive pulmonary disease).
• Uses: Scopine Di(2-thienylglycolate) (Tiotropium EP Impurity B) is a precursor to Tiotropium Bromide. Precursor to Tiotropium Bromide.

Technology Process of Scopine-2,2-dithienyl glycolate

There total 21 articles about Scopine-2,2-dithienyl glycolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) + scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5) → N-demethyltiotropium (136310-64-0)

Guidance literature:

scopolamine; With aluminum trichloride-diatomaceous earth; In cyclohexane; acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

hydroxy-di-thiophen-2-yl-acetic acid methyl ester; In cyclohexane; acetonitrile; at 65 - 70 ℃; for 3h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Molecular sieve;

Reference yield: 80.0%

(1R,3S,5S)-2'-hydroxy-2',2'-di(thiophen-2''-yl)acetic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester (136310-66-2,736108-96-6) → N-demethyltiotropium (136310-64-0)

Guidance literature:

With dihydrogen peroxide; vanadia; In N,N-dimethyl-formamide; at 57 ℃; for 4.5h;

DOI:10.1071/CH05303

Reference yield: 73.0%

hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) + scopine (498-45-3) → N-demethyltiotropium (136310-64-0)

Guidance literature:

With potassium tert-butylate; 1-butyl-3-methylimidazolium Tetrafluoroborate; In tetrahydrofuran; at 20 ℃; for 18h; Solvent; Concentration; Reagent/catalyst; Temperature; Time; Molecular sieve;

upstream raw materials:

(1R,3S,5S)-2'-hydroxy-2',2'-di(thiophen-2''-yl)acetic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

(1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol

(+/-)-Scopolamine hydrobromide

Downstream raw materials:

tiotropium bromide

C₁₀H₁₅O₄S^(1-)*C₁₉H₂₂NO₄S₂⁽¹⁺⁾

Refernces

• 1、 Issa, Fatiah,Kassiou, Michael,Chan, Hak-Kim,McLeod, Malcolm D.. "Synthesis and radiolabelling of ipratropium and tiotropium for use as PET ligands in the study of inhaled drug deposition". . p. 53 - 58. Retrieved 2006.
• 2、 -. "Preparation method of tiotropium bromide". . . Retrieved 2021/08/19.
• 3、 -. "PROCESS FOR SYNTHESIS OF TIOTROPIUM BROMIDE MONOHYDRATE". . . Retrieved 2018/09/19.