Category: 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.

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

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: (Part 1) To a stirred solution of Cinchona alkaloid (either Quinine, Quinidine, Cinchonine or Cinchonidine) (1 equiv.) in THF (0.1 M) was added the required arylmethyl halide compound (1.2 equiv.) at room temperature. The reaction mixture was refluxed overnight, cooled to room temperature and all volatiles were removed invacuo. The residue was then dissolved in CH2Cl2 (typically 2 mL for 1 mmol of starting material) and the resulting solution was added dropwise onto Et2O (typically 30 mL for 1 mmol of starting material) with vigorous stirring. The resulting precipitate was then filtered, washed thoroughly with Et2O, and further dried under high vacuum for 2 hours, yielding the intermediate alcohol product in an excellent yield. (Part2) This product (1 equiv.) was dissolved in CH2Cl2 (0.2 M). Methyl iodide (3 equiv.) and an aqueous sodium hydroxide solution (50 %w, 5 equiv.) were successively added at room temperature. The reaction mixturewas stirred at room temperature for 4 h, before water (typically 20 mL for 1 mmol of starting material) was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo (N.B: washing with brine is prohibited to avoid the I/Cl anion exchange). Purification by column chromatography on silica gel, eluting with MeOH/Acetone/CH2Cl2 (0:10:90 to 10:10:90), afforded the desired Cinchona alkaloid quaternary ammonium salt in a moderate to excellent yield.

The synthetic route of 56-54-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Antien, Kevin; Viault, Guillaume; Pouysegu, Laurent; Peixoto, Philippe A.; Quideau, Stephane; Tetrahedron; vol. 73; 26; (2017); p. 3684 – 3690;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

56-54-2, 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). 4.24.4 N-(2-F-4-Br-benzyl)quinidinium bromide (1d) Yield: 79%; white solid; m.p. 174-176 C (decomp.); [alpha]D28 +143.3 (c 0.14, CH3OH); IR (KBr): 3387, 3198, 3006, 1621, 1520, 1473, 1460, 1431, 1338, 1259, 1241, 1205, 1113, 1026, 851, 828, 719 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 8.81 (d, J = 4.4 Hz, 1H), 8.02 (d, J = 9.2 Hz, 1H), 7.87-7.76 (m, 3H), 7.67 (dd, J = 8.4, 1.6 Hz, 1H), 7.50 (dd, J = 9.2, 2.0 Hz, 1H), 7.41 (d, J = 2.4 Hz, 1H), 6.86 (d, J = 2.8 Hz, 1H), 6.51 (s, 1H), 6.03 (ddd, J = 17.2, 10.4, 6.8 Hz, 1H), 5.25-5.23 (m, 2H), 5.06 (d, J = 12.4 Hz, 1H), 4.77 (d, J = 12.4 Hz, 1H), 4.19 (t, J = 9.6 Hz, 1H), 4.06 (s, 3H), 3.97-3.85 (m, 2H), 3.44 (t, J = 11.2 Hz, 1H), 3.12 (q, J = 10.0 Hz, 1H), 2.68-2.62 (m,1H), 2.36 (t, J = 11.2 Hz, 1H), 2.00 (s, 1H), 1.82-1.75 (m, 2H), 1.10-1.03 (m, 1H); 13C NMR (100 MHz, DMSO-d6): delta = 162.1 (d, J = 252.2 Hz), 157.9, 147.9, 144.2, 143.8, 137.6, 131.9, 129.0, 125.8, 125.5 (d, J = 10.1 Hz), 121.9, 120.7, 120.3 (d, J = 25.7 Hz), 117.5, 115.4 (d, J = 13.7 Hz), 102.8, 67.9, 65.3, 56.8, 56.1, 54.7, 37.4, 26.6, 23.7, 21.0; HRMS calcd for [C33H35F6N2O2]+: 511.1391, found 511.1398.

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

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

56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,56-54-2

Phenylacetic acid (40 mg, 0.294 mmol)and quinidine (95.4 mg, 0.294 mmol) were dissolved in acetone.Crystals were obtained after 3 days. Similar crystals were obtained using ethyl methyl ketone, tetrahydrofuran, isopropanol, ethanol and methanol as solvents.

The synthetic route of 56-54-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Amombo Noa, Francoise M.; Jacobs, Ayesha; Journal of Molecular Structure; vol. 1114; (2016); p. 30 – 37;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

56-54-2,56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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). 4.24.2 N-(4-Trifluoromethylbenzyl)quinidinium bromide (1b) [25] Yield: 87%; white solid; mp 218 C (decomp.); [alpha]D28 +184.2 (c 0.15, CH3OH); IR (KBr): 3398, 3209, 2954, 1621, 1589, 1509, 1373, 1427, 1325, 1227, 1241, 1170, 1125, 1068, 1021, 1003, 934, 864, 832 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 8.82 (d, J = 4.4 Hz, 1H), 8.02 (d, J = 9.2 Hz, 1H), 7.97 (dd, J = 10.4, 9.2 Hz, 4H), 7.77 (d, J = 4.4 Hz, 1H), 7.51 (dd, J = 9.2, 2.4 Hz, 1H), 7.44 (d, J = 2.4 Hz, 1H), 6.84 (d, J = 3.6 Hz, 1H), 6.52 (s, 1H), 6.03 (ddd, J = 17.4, 10.5, 6.9 Hz, 1H), 5.25 (s, 1H), 5.10 (d, J = 8.4 Hz, 2H), 4.85 (d, J = 12.8 Hz, 1H), 4.28-4.22 (m, 1H), 4.06 (s, 3H), 4.02-4.00 (m, 1H), 3.86 (t, J = 9.4 Hz, 1H), 3.50 (t, J = 11.4 Hz, 1H), 3.00-2.90 (m, 1H), 2.69-2.63 (m, 1H), 2.40 (t, J = 11.4 Hz, 1H), 1.91 (s, 1H), 1.79-1.75 (m, 2H), 1.15-1.07 (m, 1H). 13C NMR (100 MHz, DMSO-d6): delta = 158.0, 147.9, 144.2, 143.8, 137.7, 135.1, 133.0, 131.9, 130.9 (q, J = 31.8 Hz), 126.4, 126.3, 125.9, 123.1, 121.7, 120.8, 117.5, 103.0, 68.1, 65.2, 62.9, 56.5, 56.2, 54.5, 37.2, 26.8, 23.6, 21.1.

56-54-2 (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol 637552, acatalyst-ligand compound, is more and more widely used in various fields.

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

56-54-2,56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The alkaloid (12.3 mmol, 1 eq.) and the appropriate substituted benzylic halide derivative(12.3 mmol, 1 eq.) were dissolved in THF (40 mL) with addition of a trace of NaI. The mixture washeated to reflux overnight and then cooled and stirred at ambient temperature for 1 h. In most cases theproduct precipitated as an off-white solid, but where this was not the case and the mixture containedonly a small amount of solid or no solid at all, then diethyl ether (20 mL) was added dropwise.The solid was removed via filtration and washed with THF (50 mL) or ether:THF, (1:1, v/v, 50 mL)and was dried under reduced pressure at 40 C. Where the solid formed was not a fine powder it was then taken up in DCM and this solution was then added dropwise to rapidly stirring ether (100 mL).This usually gives a finely divided solid that could be filtered and dried. (Note: The cinchonine derivedPTCs are usually very insoluble. The quinidine derived PTCs are often completely soluble at the endof the reaction.) The di(t-butyl)benzyl PTC was prepared according to the standard procedure aboveand was filtered directly from the reaction mixture.

As the paragraph descriping shows that 56-54-2 is playing an increasingly important role.

Reference£º
Article; Zhang, Tao; Scalabrino, Gaia; Frankish, Neil; Sheridan, Helen; Molecules; vol. 23; 7; (2018);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,56-54-2

To a solution of epi-quinine (232 mg, 0.71 mmol) in DMSO (5 mL) was added LiH (11.1 mg, 1.1 mmol, 1.5 equiv) and the suspension was stirred for 1 h at room temperature. Then 2-chloro-1,10-phenanthroline (181 mg, 0.84 mmol, 1.2 equiv) was added and the mixture was stirred for 18 h at room temperature and 6 h at 80?85 ¡ãC. The cooled mixture was diluted with ethyl acetate (50 mL) and washed with brine (10 ¡Á 15 mL), the solvent was removed in vacuo, and the residue purified on silica gel (CHCl3 / MeOH 10:1) to afford 246 mg (67percent) of white solid.

As the paragraph descriping shows that 56-54-2 is playing an increasingly important role.

Reference£º
Article; Zieliska-Blajet, Mariola; Boratyski, Przemyslaw J.; Sidorowicz, Lukasz; Skarzewski, Jacek; Tetrahedron; vol. 72; 21; (2016); p. 2643 – 2648;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

56-54-2,56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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). 4.24.3 N-(9-Anthrylmethyl)quinidinium chloride (1c) [26] Yield: 80%; light yellow solid; m.p. 161 C (decomp.) (lit. mp 160 C, decomp.); [alpha]D28 +390.0 (c 0.12, CH3OH); IR (KBr): 3394, 3183, 1621, 1508, 1458, 1473, 1431, 1258, 1362, 1240, 1227, 1029, 922, 864, 744 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 8.98 (s, 1H), 8.86 (d, J = 4.4 Hz, 1H), 8.79 (d, J = 9.2 Hz, 1H), 8.70 (d, J = 9.2 Hz, 1H), 8.28 (dd, J = 8.2, 3.0 Hz, 2H), 8.05 (d, J = 9.2 Hz, 1H), 7.90 (d, J = 4.4 Hz, 1H), 7.82-7.74 (m, 3H), 7.69-7.64 (m, 3H), 7.53 (dd, J = 7.6, 2.4 Hz, 1H), 6.98 (s, 1H), 6.33 (d, J = 14.4 Hz, 1H), 6.03 (ddd, J = 17.2, 10.2, 7.2 Hz, 1H), 5.88 (d, J = 14.0 Hz, 1H), 5.18 (d, J = 10.4 Hz, 1H), 5.08 (d, J = 17.2 Hz, 1H), 4.46 (t, J = 9.2 Hz, 2H), 4.21 (s, 4H), 3.18 (t, J = 11.2 Hz, 1H), 2.62-2.54 (m, 1H), 2.46-2.35 (m,2H), 1.78 (s, 1H), 1.69 (d, J = 8.4 Hz, 1H), 1.56-1.53 (m, 1H), 1.10-1.04 (m, 1H); 13C NMR (100 MHz, DMSO-d6): delta = 157.9, 147.9, 144.3, 137.9, 133.5, 133.3, 132.5, 131.8, 131.7, 131.6, 130.2, 128.3, 128.0, 126.1, 126.0, 125.3, 125.0, 122.3, 121.0, 119.3, 117.5, 103.2, 67.9, 65.7, 56.5, 56.1, 55.8, 55.6, 37.7, 26.1, 24.2, 21.6.

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