2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

Base Information

• Chemical Name: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester
• CAS No.: 320347-97-5
• Molecular Formula: C17H19NO3S2
• Molecular Weight: 349.475
• Mol file: 320347-97-5.mol

Synonyms:2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester;(R)-Quinucldin-3-yl hydroxybis(2-thienyl)acetate;2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester-5

Chemical Property of 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

Chemical Property:

• Melting Point: 180℃ (isopropyl ether )
• Boiling Point: 513.3±50.0 °C(Predicted)
• PKA: 10.33±0.29(Predicted)
• PSA: 106.25000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 2.62080

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Quinuclidinyldi(2-thienyl)glycolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-3-Quinuclidinyl di(2-thienyl)glycolate acts as a potent and long-acting muscarinic antagonist with minimal systemic exposure after inhalation. Used in the treatment of chronic obstructive pulmonary disease.

Technology Process of 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

There total 17 articles about 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester 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: 89.05%

2-hydroxy-2,2-di(thiophen-2-yl)acetic acid (4746-63-8) + (R)-quinuclidin-3-ol (25333-42-0) → hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester (320347-97-5)

Guidance literature:

(R)-quinuclidin-3-ol; With sodium methylate; In cyclohexane; at 80 - 85 ℃; Large scale;

2-hydroxy-2,2-di(thiophen-2-yl)acetic acid; In cyclohexane; at 80 - 85 ℃; Large scale;

Reference yield: 80.5%

hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) + (R)-quinuclidin-3-ol (25333-42-0) → hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester (320347-97-5)

Guidance literature:

With sodium methylate; In cyclohexane; at 85 ℃; for 1h; Temperature; Solvent;

Reference yield: 80.0%

(R)-quinuclidin-3-yl (tert-butyldimethylsilyl)-2,2-di(thiophene-2-yl)acetate → hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester (320347-97-5)

Guidance literature:

With hydrogenchloride; methanol; In water; at 0 - 10 ℃;

upstream raw materials:

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

(R)-quinuclidin-3-ol

Ethyl (2,2'-Dithienyl)glycolate

(+)-Aceclidine

Downstream raw materials:

(R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride

(3R)-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-(4-phenylbutyl)-1-azoniabicyclo[2.2.2]octane bromide

(3R)-1-benzyl-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide

aclidinium bromide

Refernces

• 1、 -. "Novel method for synthesis and purification of aclidinium bromide". Page/Page column 6-9. . Retrieved 2018/12/05.
• 2、 -. "A PROCESS FOR PREPARING ACLIDINIUM BROMIDE AND INTERMEDIATES THEREOF". . . Retrieved 2018/09/12.