Tiotropium EP Impurity D

Base Information

• Chemical Name: Tiotropium EP Impurity D
• CAS No.: 136310-66-2
• Molecular Formula: C18H19NO3S2
• Molecular Weight: 361.486
• European Community (EC) Number: 603-954-1
• DSSTox Substance ID: DTXSID501120860
• Wikidata: Q76416756
• Mol file: 136310-66-2.mol

Synonyms:136310-66-2;Tiotropium EP Impurity D;[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-yl acetate;Tiotropium Bromide Monohydrate Impurity D;SCHEMBL16742011;WUOOUIFCFAXEKJ-PBWFPOADSA-N;DTXSID501120860;MFCD26143006;PD160506;(1R,3S,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-dithiophen-2-ylacetate;endo-?-Hydroxy-?-2-thienyl-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-y Ester 2-Thiopheneacetic Acid;Di(2-thienyl)glycolic Acid Tropenol Ester;(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

Chemical Property of Tiotropium EP Impurity D

Chemical Property:

• Boiling Point: 522.8±50.0 °C(Predicted)
• PKA: 10.33±0.29(Predicted)
• PSA: 106.25000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 2.92780
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 361.08063582
• Heavy Atom Count: 24
• Complexity: 494

Purity/Quality:

98% ^*data from raw suppliers

rel-(1R,3S,5S)-8-Methyl-8-azabicyclo[3,2,1]oct-6-en-yl-2-hydroxy-2,2-dithiophen-2-ylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(CC1C=C2)OC(=O)C(C3=CC=CS3)(C4=CC=CS4)O
• Isomeric SMILES: CN1[C@@H]2CC(C[C@H]1C=C2)OC(=O)C(C3=CC=CS3)(C4=CC=CS4)O
• 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.

Technology Process of Tiotropium EP Impurity D

There total 6 articles about Tiotropium EP Impurity D 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: 83.0%

hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) + (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol (20513-09-1) → (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)

Guidance literature:

With sodium hydride; In toluene; at 25 - 75 ℃; for 8h;

Reference yield:

tropenol (22143-95-9) + 1-hydroxy-1,1-bis(thiophen-2-yl)butan-2-one → (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)

Guidance literature:

tropenol; 1-hydroxy-1,1-bis(thiophen-2-yl)butan-2-one; With triethylamine; In tetrahydrofuran; ethanol; at 30 - 60 ℃; for 1h;

With sodium ethanolate; In tetrahydrofuran; ethanol; at 60 ℃; for 5h;

Reference yield:

hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) + tropenol (22143-95-9) → (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)

Guidance literature:

hydroxy-di-thiophen-2-yl-acetic acid methyl ester; tropenol; In toluene; at 30 - 60 ℃; for 1h;

With sodium hydride; In toluene; at 60 ℃; for 5h;

upstream raw materials:

hydroxy-di-thiophen-2-yl-acetic acid methyl ester

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

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

(+/-)-Scopolamine hydrobromide

Downstream raw materials:

tiotropium bromide

N-demethyltiotropium