(S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

Base Information

• Chemical Name: (S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• CAS No.: 51743-68-1
• Molecular Formula: C20H26N2O2
• Molecular Weight: 326.439
• European Community (EC) Number: 215-862-5
• Wikipedia: Dihydroquinidine
• Mol file: 51743-68-1.mol

Synonyms:dihydroquinidine;dihydroquinine;hydroquinidine;hydroquinidine dihydrochloride, (1beta,4beta,3S)-(+-)-isomer;hydroquinidine dihydrochloride, (3alpha,9S)-(+-)-isomer;hydroquinidine hydrochloride;hydroquinidine monosulfate;hydroquinidine monosulfate, (1beta,3alpha,4beta,8alpha,9R)-isomer;hydroquinidine monosulfate, (1beta,3alpha,4beta,9S)-isomer;hydroquinidine sulfate;hydroquinidine sulfate, (9S)-isomer;hydroquinidine, (+-)-isomer;hydroquinidine, (1beta, 3alpha,4beta,8alpha,9R)-isomer;hydroquinidine, (1beta,3alpha,4beta,9S)-isomer;hydroquinidine, (1beta,4beta,9S)-(+-)-isomer;hydroquinidine, (3alpha,9S)-(+-)-isomer;hydroquinidine, (8alpha,9R)-isomer;hydroquinidine, (8alpha,9S)-isomer;hydroquinidine, (9R)-isomer;hydroquinidine, (9S)-(+-)-isomer;hydroquinine;LCN 834;LCN-834;Lentoquine;Sérécor

Chemical Property of (S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

Chemical Property:

• PSA: 45.59000
• LogP: 3.33510
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 326.199428076
• Heavy Atom Count: 24
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)O
• Recent ClinicalTrials: Hydroquinidine Versus Placebo in Patients With Brugada Syndrome

Technology Process of (S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

There total 21 articles about (S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol 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: 99.0%

qunidine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → epi-dihydroquinine (522-66-7,1435-55-8,14645-32-0,23495-98-9,26666-96-6,47342-32-5,47342-33-6,51049-33-3,51049-34-4,66182-83-0,66182-84-1,51743-68-1)

Guidance literature:

With sulfuric acid; hydrogen; palladium dichloride; at 20 ℃; for 4h; under 3040.2 Torr;

DOI:10.1039/c2ob25832c

Reference yield: 76.0%

9-mesyloxydihydroquinine (889449-48-3) → epi-dihydroquinine (522-66-7,1435-55-8,14645-32-0,23495-98-9,26666-96-6,47342-32-5,47342-33-6,51049-33-3,51049-34-4,66182-83-0,66182-84-1,51743-68-1)

Guidance literature:

With L-Tartaric acid; for 3h; Heating;

DOI:10.1055/s-2006-926382

Reference yield:

(1S,4S,5R,E)-5-ethyl-2-[(6-methoxyquinolin-4-yl)methylene]quinuclidine → epi-dihydroquinine (51743-68-1) + dihydroquinidine (1435-55-8) + dihydroquinine (522-66-7) + epi-dihydroquinidine (14645-32-0)

Guidance literature:

(1S,4S,5R,E)-5-ethyl-2-[(6-methoxyquinolin-4-yl)methylene]quinuclidine; With 5 mol% Pd/C; hydrogen; In methanol; at 20 ℃; for 1h;

With sodium hydride; In dimethyl sulfoxide; mineral oil; at 70 ℃; for 0.0166667h;

With oxygen; In dimethyl sulfoxide; mineral oil; at 70 ℃; for 0.75h;

DOI:10.1002/ejoc.201403099

upstream raw materials:

hydrogenchloride

4-bromo-6-methoxyquinoline

6'-methoxycinchonan-9-ol

9-mesyloxydihydroquinine

Downstream raw materials:

(8S,9R)-9-Benzoyloxy-6'-methoxy-10,11-dihydro-cinchonan

6'-Methoxy-9-(4-nitro-benzoyloxy)-10,11-dihydro-cinchonan

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

Dihydroquinidine 4-vinylbenzoate

Refernces

• 1、 Breman, Arjen C.,Ruiz-Olalla, Andrea,Van Maarseveen, Jan H.,Ingemann, Steen,Hiemstra, Henk. "Synthesis of Quinuclidines by Intramolecular Silver-Catalysed Amine Additions to Alkynes". . p. 7413 - 7425. Retrieved 2016/02/20.
• 2、 Zielinska-Blajet, Mariola,Kucharska, Malgorzata,Skarzewski, Jacek. "Simple enantiospecific synthesis of sulfides of Cinchona alkaloids". . p. 1176 - 1182. Retrieved 2007/10/03.