Month: October 2020

Ethyl quinuclidine-4-carboxylate, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”22766-68-3

Example 27 Preparation of 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol A solution of 2-thienyllithium (1.0M in THF, 9.10 mL, 9.10 mmol) was chilled down to -30 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.4196 g, 2.289 mmol) in THF (8 mL) was slowly added to the reaction mixture over 20 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with water and then evaporated to dryness. H2O and DCM were added, causing a light brown solid to crash out. This solid was filtered off to give the title compound (0.4161 g, 59.5%). EI-MS m/z 306(M+H+) Rt (1.35 min).

The chemical industry reduces the impact on the environment during synthesis, Ethyl quinuclidine-4-carboxylate, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.22766-68-3, Ethyl quinuclidine-4-carboxylate it is a common compound, a new synthetic route is introduced below.22766-68-3

1-azabicyclo[2.2.2]oct-4-yl[bis(3-fluorophenyl)]methanol A solution of 3-fluorophenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1756 g, 0.958 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0 C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60 C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.242 g, 76.7%). EI-MS m/z 330(M+H+) Rt (1.45 min).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Ethyl quinuclidine-4-carboxylate reaction routes.

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.40117-63-3, Quinuclidine-4-carboxylic acid hydrochloride it is a common compound, a new synthetic route is introduced below.40117-63-3

1. Preparation of 3-fluorobenzyl quinuclidine-4-carboxylate (Compound 91). A mixture of quinuclidine-4-carboxylic acid hydrochloride (100 mg, 0.52 mmol) and thionyl chloride (500 mul, 6.85 mmol) was refluxed for 2 hours. The reaction was cooled to room temperature, and the solvent was accurately removed. The residue was suspended in dry DCM and treated with (3-fluorophenyl)methanol (65.8 mg, 0.52 mmol). The reaction was stirred at room temperature for 24 hours. The solvent was evaporated, and the residue was dissolved in water (1 ml), basified with NaHCO3 and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated to obtain 3-fluorobenzyl quinuclidine-4-carboxylate (41 mg, 29.8% yield), which was used in the next step without any further purification.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Quinuclidine-4-carboxylic acid hydrochloride reaction routes.

Reference£º
Patent; Chiesi Farmaceutici S.p.A.; US2012/276018; (2012); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”22766-68-3

1-azabicyclo[2.2.2]oct-4-yl{bis[3-(methyloxy)phenyl]}methanol A solution of 3-(methyloxy)phenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1608 g, 0.877 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0 C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60 C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.2881 g, 92.9%). EI-MS m/z 354(M+H+) Rt (1.46 min)., 22766-68-3

The chemical industry reduces the impact on the environment during synthesis, Ethyl quinuclidine-4-carboxylate, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.22766-68-3, Ethyl quinuclidine-4-carboxylate it is a common compound, a new synthetic route is introduced below.22766-68-3

Step 1. A solution of 4-carbethoxyquinuclidine (10.92 g) in THF (155 mL) was treated at-780C with borane-THF (1.0 M, 77.5 mL). The resulting mixture was stirred at -78C for 4 h, then treated with water (50 mL), warmed to room temperature and stirred for an additional hour. The reaction mixture was diluted with ethyl acetate and the aqueous phase was separated and extracted with two further portions of ethyl acetate. The combined organic layers were washed with brine- (twice), dried (MgSO4), filtered and evaporated in vacuo. Purification by silica gel chromatography (eluting with cyclohexane-ethyl acetate [1 :0 to 1 :1]) gave 1-boranyl-1-aza-bicyclo[2.2.2]octane-4- carboxylic acid ethyl ester (7.12 g, 61%) as an off-white solid. 1H NMR (400 MHz, CDCI3) delta 4.16 (2H1 q, J = 6.9), 3.10-3.05 (6H1 m), 1.98-1.93 (6H, m), 1.26 (3H, t, J = 6.9)., 22766-68-3

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Ethyl quinuclidine-4-carboxylate reaction routes.

Reference£º
Patent; ARGENTA DISCOVERY LIMITED; WO2008/99186; (2008); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”22766-68-3

To a solution of ethyl 1-aza-bicyclo[2.2.2]octane-4-carboxylate (PCT2005104745) (9.610 g, 52.44 mmol) in THF (480 ml) at -780C was added borane-THF complex (73.41 ml,73.41 mmol) and the resulting solution was stirred at this temperature for 3.5 h. The reaction was quenched with slow addition of H2O (50 ml), warmed to RT, and allowed to stir for 45 min. The solution was diluted with EtOAc (100 ml), washed with brine (15 ml), extracted with EtOAc (3 x 50 ml), dried (Na2SO4) and evaporated. The crude product was purified on a CombiFlash companion using 0-50% EtOAc in cyclohexane as eluent to give a bright yellow solid.Yield: 7.236 g (70%)1 H NMR (400 MHz, CDCI3) delta = 4.15 (q, 2H), 3.07 (t, 4H)1 1.96 (t, 4H), 1.26 (t, 3H) ppm.

The chemical industry reduces the impact on the environment during synthesis, Ethyl quinuclidine-4-carboxylate, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; ARGENTA DISCOVERY LIMITED; WO2009/60206; (2009); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

22766-68-3, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”22766-68-3

In a 500 mL three-necked flask, phenyllithium (160 mL, lM in THF) was treated with nitrogen Was slowly added dropwise to a solution of compound 1-4 (6.8 g, 0.04momicron1) in tetrahydrofuran (120 mL) Control the temperature at -50 C and stir at room temperature overnight. Water (200 mL) was added to quench the reaction, Extracted with ethyl acetate (500 mL), the organic layer was washed with saturated brine, dried over sodium sulfate, The solvent was evaporated under reduced pressure to give 6.8 g of a brown viscous solid, Ethyl acetate: petroleum ether = 1: 2 (200 mL) was added and stirred at room temperature for 2 h, filtered, The filter cake was washed with petroleum ether and dried to give a 5.1g lime light gray solid.

The chemical industry reduces the impact on the environment during synthesis, 22766-68-3, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Yifang Bio-technology (Shanghai) Co., Ltd.; Dai Xing; Jiang Yueheng; Wang Yaolin; (26 pag.)CN107200734; (2017); A;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.40117-63-3, Quinuclidine-4-carboxylic acid hydrochloride it is a common compound, a new synthetic route is introduced below.40117-63-3

Under the protection of nitrogen, a solution for dissolving the WD2 with the tetrahydrofuran is added into a 20-liter reaction kettle, the temperature is controlled to be below 40 C under stirring, and 3.8 liters of phenylmagnesium bromide reagent is added dropwise, and carrying out heating reflux reaction for 4 hours. The temperature is controlled to be controlled at 40 C under cooling and stirring, and 1.547 kg of ammonium chloride aqueous solution (25%) is added dropwise) after dropwise adding, adding about 74 kg of purified water, and standing for liquid separation after stirring, so as to obtain an organic phase; extracting the water phase by using 2-methyl tetrahydrofuran, the organic phase is combined with the organic phase, and the organic phase is washed with a 25% sodium chloride aqueous solution. A 1 m hydrochloric acid aqueous solution is added to the obtained organic phase to be about 140Kg, fully stirring, standing and separating liquid to obtain a water phase; dropwise adding a sodium hydroxide aqueous solution with the concentration of 4 m into the obtained hydrochloric acid salt water solution of the WD1 to adjust the pH value, and separating out solids. After dropping, stirring is continued for about 0.5 hour, and the mixture is filtered to obtain a filter cake; the filtrate is subjected to reduced pressure concentration until no large amount of distillate is discharged, and the filtrate is filtered to obtain a filter cake; combining the obtained filter cakes twice, and washing with purified water with the temperature of 25 +/-5 C, and then pulping is carried out by using purified water at 25 +/-5 C for about 2.61 kg. The filter cake is firstly washed with purified water at 25 +/-5 C, and then is dried to obtain WD1:

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Quinuclidine-4-carboxylic acid hydrochloride reaction routes.

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Yi Shixu; Fu Li; (6 pag.)CN106810546; (2017); A;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”22766-68-3

1-azabicyclo[2.2.2]oct-4-yl[bis(3-fluorophenyl)]methanol A solution of 3-fluorophenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1756 g, 0.958 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0 C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60 C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.242 g, 76.7%). EI-MS m/z 330(M+H+) Rt (1.45 min).

The chemical industry reduces the impact on the environment during synthesis, Ethyl quinuclidine-4-carboxylate, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.40117-63-3, Quinuclidine-4-carboxylic acid hydrochloride it is a common compound, a new synthetic route is introduced below.40117-63-3

(Quinuclidin-4-yl)carboxylic acid was prepared from 4-cyanoquinuclidine (Oakwood Products) following the procedure of Grob and Renk, Helv. Chim. Acta, 37, 1681 (1954). To a stirred suspension of quinuclidine-4-carboxylic acid hydrochloride (100 mg, 0.523 mmol) in 3 mL of anhydrous tetrahydrofuran at 0 C. was added borane methylsulfide complex (42 mg, 0.553 mmol). The mixture was stirred at room temperature for 1 hr and heated to reflux overnight. The reaction was cooled to 0 C. and carefully treated with 1 mL of methanol. The solvent was then removed under reduced pressure to leave the desired alcohol. Yield 36 mg. MS (m/e): 141.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Quinuclidine-4-carboxylic acid hydrochloride reaction routes.

Reference£º
Patent; CoMentis, Inc.; BILCER, Geoffrey M.; NG, Raymond; (104 pag.)US2016/9706; (2016); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider