56-54-2,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.
General procedure: To a flame-dried flask equipped with a magnetic stirring bar and a condenser was added with cinchona alkaloids (1 mmol), toluene (5 mL), and benzyl bromide derivatives (1.2 mmol, 1.2 equiv.). The mixture was heated at 80 8C until a TLC analysis showing that the starting material was completely consumed. Cooled to room temperature and poured onto Et2O (30 mL) with stirring, the resulting suspension was stirred for another 1 h. Then the precipitate was purified by flash chromatography (MeOH/EtOAc = 1/10, V/V). 4.24.6 N-(3,5-Ditrifluoromethylbenzyl)quinidinium bromide (1f) [27] Yield: 85%; white solid; mp 177 C (decomp.); [alpha]D28 +176.1 (c 0.19, CH3OH); IR (KBr): 3394, 3201, 2954, 2664, 1622, 1509, 1473, 1432, 1374, 1281, 1214, 1226, 1178, 1135, 1027, 1005, 866, 905, 843, 828, 709, 682 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 8.82 (d, J = 4.8 Hz, 1H), 8.56 (s, 2H), 8.38 (s, 1H), 8.04 (d, J = 9.2 Hz, 1H), 7.77 (d, J = 4.4 Hz, 1H), 7.53 (dd, J = 7.2, 2.4 Hz 1H), 7.44 (d, J = 2.4 Hz, 1H), 6.78 (d, J = 3.2 Hz, 1H), 6.48 (s, 1H), 6.04 (ddd, J = 17.4, 10.2, 7.2 Hz, 1H), 5.28 (d, J = 2.8 Hz, 1H), 5.22 (d, J = 12.4 Hz, 2H), 5.01 (d, J = 12.8 Hz, 1H), 4.34 (t, J = 10.0 Hz, 1H), 4.10-4.13 (m, 1H), 4.06 (s, 3H), 3.80 (t, J = 9.4 Hz, 1H), 3.48 (t, J = 11.4 Hz, 1H), 3.04 (q, J = 9.6 Hz, 1H), 2.62 (q, J = 8.4 Hz, 1H), 2.42 (t, J = 11.6 Hz, 1H), 1.91 (s, 1H), 1.85-1.72 (m, 2H), 1.20-1.13 (m, 1H); 13C NMR (100 MHz, DMSO-d6): delta = 158.1, 147.9, 144.2, 143.7, 137.8, 135.1, 132.0, 131.7, 131.3 (q, J = 33.1 Hz), 130.1, 126.0, 125.0, 124.6 (q, J = 4.1 Hz), 123.7 (q, J = 271.3 Hz), 121.5, 120.9, 117.6, 103.1, 68.4, 65.2, 61.8, 56.3, 56.2, 54.7, 37.4, 26.9, 23.6, 21.1.
The synthetic route of 56-54-2 has been constantly updated, and we look forward to future research findings.
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