(3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate

Base Information

• Chemical Name: (3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate
• CAS No.: 62869-69-6
• Deprecated CAS: 70135-17-0,4478-53-9,160902-51-2
• Molecular Formula: C21H23NO3
• Molecular Weight: 337.419
• European Community (EC) Number: 636-310-3
• UNII: E69DLR7470,VF416M2D3P
• Nikkaji Number: J419.449G
• Wikidata: Q27464767
• Pharos Ligand ID: M6RA89DLSTZB
• ChEMBL ID: CHEMBL558910
• Mol file: 62869-69-6.mol

Synonyms:62869-69-6;(R)-(-)-QNB;Quinuclidinyl benzilate, (-)-;(3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate;(R)-Quinuclidinyl benzilate;(-)-Quinuclidinyl benzilate;UNII-VF416M2D3P;VF416M2D3P;CHEMBL558910;E69DLR7470;[(3R)-1-azabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-diphenylacetate;Benzilic acid, 3-quinuclidinyl ester;(R)-(-)-3-Quinuclidinyl benzilate;Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, 1-azabicyclo(2.2.2)oct-3-yl ester, (-)-;Buzz;Agent BZ;3-Chinuclidylbenzilate;3-Quinuclidyl benzilate;3-Quinuclidinol benzilate;3-Oxyquinuclidine benzilate;QNB;.beta.-Quinuclidinyl benzilate;3-Hydroxyquinuclidine benzilate;(R)-QNB;3-Quinuclidinol, benzilate (ester);(R)-3-Quinuclidinyl Benzilate;Agent Buzz;CS 4030;EA 2277;NSC 173698;NSC-173698;1-Azabicyclo(2.2.2)octan-3-ol, benzilate;BZ [anticholinergic];SCHEMBL241173;UNII-E69DLR7470;HSDB 7533;Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, 1-azabicyclo(2.2.2)oct-3-yl ester;HGMITUYOCPPQLE-IBGZPJMESA-N;BDBM50450592;QUINUCLIDINYL BENZILATE, (R)-;(-)-3-QUINUCLIDINYL BENZILATE;QUINUCLIDINYL BENZILATE, (+/-)-;RO-2-3308;FT-0773200;3-(2,2-Diphenyl-2-hydroxyethanoyloxy)-quinuclidine;Q27464767;3-QUINUCLIDINOL DL-FORM BENZILATE (ESTER) [MI];(R)-QUINUCLIDIN-3-YL 2-HYDROXY-2,2-DIPHENYLACETATE;2,2-DIPHENYL-2-HYDROXYACETIC ACID 3-QUINUCLIDINYL ESTER;hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo [2.2.2]oct-3-yl) ester;hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo [2.2.2]oct-3-yl)ester;Hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester;hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester;hydroxydiphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester;hydroxyl-diphenyl-acetic acid(r)-(1-aza-bicyclo-[2.2.2]oct-3-yl)ester;BENZENEACETIC ACID, .ALPHA.-HYDROXY-.ALPHA.-PHENYL-, (3R)-1-AZABICYCLO(2.2.2)OCT-3-YL ESTER

Chemical Property of (3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate

Chemical Property:

• Melting Point: 164oC
• PSA: 49.77000
• LogP: 2.49780
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 337.16779360
• Heavy Atom Count: 25
• Complexity: 442

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-(?)-3-Quinuclidinyl benzilate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
• Isomeric SMILES: C1CN2CCC1[C@H](C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
• Uses: (R)-(-)-3-Quinuclidinyl benzilate is a pharmacological agent used as muscarinic M3 antagonist for the inhaled treatment of chronic obstructive pulmonary disease (COPD).

Technology Process of (3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate

There total 3 articles about (3r)-1-Azabicyclo[2.2.2]oct-3-Yl Hydroxy(Diphenyl)acetate 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: 35.0%

(3R)-1-azabicyclo[2.2.2]oct-3-yl oxo(phenyl)acetate (141831-51-8) + phenyllithium (591-51-5) → (R)-(-)-3-quinuclidinyl benzilate (62869-69-6)

Guidance literature:

(3R)-1-azabicyclo[2.2.2]oct-3-yl oxo(phenyl)acetate; phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; at -40 - 20 ℃;

With water; ammonium chloride; In tetrahydrofuran; diethyl ether; cyclohexane;

DOI:10.1021/jm900132z

Reference yield:

methyl benzilate (76-89-1) + (R)-quinuclidin-3-ol (25333-42-0) → (R)-(-)-3-quinuclidinyl benzilate (62869-69-6)

Guidance literature:

With sodium hydride; In toluene; for 3h; Inert atmosphere; Reflux;

Reference yield:

(R)-quinuclidin-3-ol (25333-42-0) + ethyl benzilate (52182-15-7) → (R)-(-)-3-quinuclidinyl benzilate (62869-69-6)

Guidance literature:

With sodium; Yield given. Multistep reaction; 1) benzene, 30 min, reflux; 2) benzene, reflux, 30 min;

DOI:10.1021/jm00402a035

upstream raw materials:

(R)-quinuclidin-3-ol

ethyl benzilate

methyl benzilate

(3R)-1-azabicyclo[2.2.2]oct-3-yl oxo(phenyl)acetate

Downstream raw materials:

fluoro-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

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

(3R)-3-{[hydroxy(diphenyl)acetyl]oxy}-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide