Ethyl quinuclidine-4-carboxylate

Base Information

• Chemical Name: Ethyl quinuclidine-4-carboxylate
• CAS No.: 22766-68-3
• Molecular Formula: C10H17NO2
• Molecular Weight: 183.25
• Hs Code.: 2933990090
• European Community (EC) Number: 807-704-4
• DSSTox Substance ID: DTXSID20341487
• Nikkaji Number: J99.417K
• Wikidata: Q82111711
• Mol file: 22766-68-3.mol

Synonyms:Ethyl quinuclidine-4-carboxylate;22766-68-3;ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate;Ethyl 4-quinuclidinecarboxylate;1-Azabicyclo[2.2.2]octane-4-carboxylic acid, ethyl ester;4-Quinuclidinecarboxylic acid, ethyl ester;MFCD19686937;1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester;EthylQuinuclidine-4-carboxylate;4-(Ethoxycarbonyl)quinuclidine;SCHEMBL3220818;DTXSID20341487;ethyl quinucli-dine-4-carboxylate;Ethyl quinuclidine-4-carboxylate #;AMY30051;CS-M1578;SB17914;DS-17374;SY033082;Quinuclidine-4-carboxylic acid ethyl ester;FT-0702092;F11935;A878449;1-Azabicyclo[2.2.2]octane-4-carboxylic acid,ethyl ester

Chemical Property of Ethyl quinuclidine-4-carboxylate

Chemical Property:

• Boiling Point: 233.4±40.0 °C(Predicted)
• PKA: 9.44±0.12(Predicted)
• PSA: 29.54000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 0.97330
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 183.125928785
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl4-Quinuclidinecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C12CCN(CC1)CC2
• Uses: Ethyl 4-Quinuclidinecarboxylate is a reactant used in the synthesis of azoniabicyclooctanes as muscarinic acetylcholine receptor antagonists.

Technology Process of Ethyl quinuclidine-4-carboxylate

There total 9 articles about Ethyl quinuclidine-4-carboxylate 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: 99.4%

1-(2-chloroethyl)-4-piperidinecarboxylic acid ethyl ester (869112-14-1) → azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester (22766-68-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -50 - 20 ℃; for 16.4167h; Solvent; Inert atmosphere;

Reference yield:

ethyl 1-(2-chloroethyl)piperidine-4-carboxylate hydrochloride → azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester (22766-68-3)

Guidance literature:

ethyl 1-(2-chloroethyl)piperidine-4-carboxylate hydrochloride; With potassium carbonate; In water; toluene; for 0.166667h;

With potassium hexamethylsilazane; In toluene; at 40 ℃; for 2h;

Reference yield:

1-azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester hydrochloride (22766-67-2) → azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester (22766-68-3)

Guidance literature:

With sodium hydroxide; In water; toluene; at 20 ℃; for 0.166667h;

upstream raw materials:

1-(2-chloroethyl)-4-piperidinecarboxylic acid ethyl ester

ethyl-4-(2-chloroethyl)-piperidine-4-carboxylate hydrochloride

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

4-carbethoxypiperidine

Downstream raw materials:

quinuclidine-4-carbaldehyde

4-[hydroxy(diphenyl)methyl]-1-(2-hydroxyethyl)-1-azoniabicyclo[2.2.2]octane bromide

1-azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester hydrochloride

α,α-diphenyl-1-azabicyclo[2.2.2]octane-4-methanol

Refernces

• 1、 -. "Preparation method of umeclidinium bromide intermediate". Paragraph 0028; 0029; 0038; 0039; 0044; 0045. . Retrieved 2021/04/14.
• 2、 -. "PROCESS FOR THE PREPARATION OF UMECLIDINIUM BROMIDE". Page/Page column 13. . Retrieved 2018/05/27.