O-Desmethyl Quinidine

Base Information

• Chemical Name: O-Desmethyl Quinidine
• CAS No.: 70877-75-7
• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.396
• Mol file: 70877-75-7.mol

Synonyms:6'-Hydroxycinchonine;Cupreidine;O-Demethylquinidine;O-Desmethylquinidine;

Chemical Property of O-Desmethyl Quinidine

Chemical Property:

• Melting Point: 186-190 °C
• Boiling Point: 514.572 °C at 760 mmHg
• PKA: 8.82±0.40(Predicted)
• Flash Point: 265.004 °C
• PSA: 56.59000
• Density: 1.286 g/cm³
• LogP: 2.80810
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of O-Desmethyl Quinidine

There total 9 articles about O-Desmethyl Quinidine 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%

Quinine (130-95-0) → 4-[(R)-((2S,4S,5R)-5-ethenyl-1-azabicyclo-[2.2.2]octan-2-yl)(hydroxy)methyl]quinolin-6-ol (524-63-0,70877-75-7)

Guidance literature:

With sodium hydride; ethanethiol; In N,N-dimethyl-formamide; mineral oil; at 110 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201901219

Reference yield: 99.0%

quinine (130-95-0) → (3ξ,8α,9R)-cinchonan-6',9-diol (524-63-0,70877-75-7)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Inert atmosphere;

Reference yield: 93.0%

→ 4-[(R)-((2S,4S,5R)-5-ethenyl-1-azabicyclo-[2.2.2]octan-2-yl)(hydroxy)methyl]quinolin-6-ol (524-63-0,70877-75-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 40 ℃; Inert atmosphere;

With ammonium hydroxide; water; In dichloromethane; at 0 ℃;

upstream raw materials:

quinindine

qunidine

quinine

quinine 9O-methanesulfonate

Downstream raw materials:

Quinine

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

(R)-[(1S,2S,4S)-5-Eth-(Z)-ylidene-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methanol

dihydroquinine

Refernces

• 1、 Trenti, Francesco,Yamamoto, Kotaro,Hong, Benke,Paetz, Christian,Nakamura, Yoko,O'Connor, Sarah E.. "Early and Late Steps of Quinine Biosynthesis". supporting information. p. 1793 - 1797. Retrieved 2021/04/05.
• 2、 Huang, Yong-Shuang,Song, Shuang-Gui,Ren, Lei,Li, You-Gui,Wu, Xiang. "Enantioselective γ-Alkylation of α,β-Unsaturated Aldehydes Using New Cinchona-Based Primary Amine Catalyst". supporting information. p. 6838 - 6841. Retrieved 2019/11/11.