With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.56-54-2,(S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol,as a common compound, the synthetic route is as follows.
56-54-2, General procedure: 4.24.13 N-(3,5-Ditrifluoromethyl)benzyl-9-O-benzyl-6′-hydroxyquinidinium bromide (4d) Sodium hydride (96.0 mg, 4.0 mmol) was added to a solution of quinidine (324.4 mg, 1.0 mmol) in dry DMF (5 mL). Benzyl chloride (173 muL, 1.5 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 20 h and quenched by water. The aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo to afford yellowish oil, which was used without purification. Ethanethiol (434.0 muL, 5.8 mmol) was added to a stirred suspension of sodium hydride (139.3 mg, 5.8 mmol) in dry DMF (3 mL). The yellowish oil (300 mg) in dry DMF (3 mL) was added dropwise and the reaction mixture was stirred at 110 C for 15 h. The solvent and excess ethanethiol were removed under reduced pressure. The crude product was added the 3,5-ditrifluoromethylbenzyl bromide (336.2 mg, 1.1 mmol) in THF (6 mL). The reaction mixture was refluxed and monitored by TLC analysis. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (MeOH/EtOAc = 1/20, V/V). The product was obtained as pale white solid.
As the paragraph descriping shows that 56-54-2 is playing an increasingly important role.
Reference£º
Article; Wu, Shaoxiang; Guo, Jiyi; Sohail, Muhammad; Cao, Chengyao; Chen, Fu-Xue; Journal of Fluorine Chemistry; vol. 148; (2013); p. 19 – 29;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI