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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 reaction routes of Ethyl quinuclidine-4-carboxylate, 22766-68-3

22766-68-3, 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. Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3,the quinuclidine compound, it is a common compound, a new synthetic route is introduced below.

Example 13: Preparation of 4-[cyano(di-2-thienyl)methyl]-1-[3- (DhenVIoxVlDroDVIl-1-azoniabicvclo [2.2.210ctane bromide;. 1-Azabicyclof2. 2. 2 Joct-4-yl(di-2-thienyl)methanol; A solution of 2-thienyllithium (1.0 M in THF, 13.0 mL, 13 mmol) was chilled down to -30 C under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.77 g, 4.20 mmol) in THF (12 mL) was slowly added to the 2-thienyllithium at-30 C over 40 min. The reaction was allowed to warm up to room temperature for overnight. The reaction was quenched with H20 and then diluted with EtOAC, hexane and DCM causing a solid to crash out of solution. The solid was filtered off, resulting in the desired compound (0.9132 g, 71.3%). EI-MS m/z 306 (M+) Rt (1.33 min).

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/112644; (2005); A2;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Application of 3-Bromo-1,5-naphthyridine

40117-63-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,40117-63-3 ,Quinuclidine-4-carboxylic acid hydrochloride, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to quinuclidine compound, name is Quinuclidine-4-carboxylic acid hydrochloride, and cas is 40117-63-3, its synthesis route is as follows.

Under the protection of nitrogen, phenyllithium (1.5 – 1.7M cyclohexane/diethyl ether solution (70:30), 30.0 ml, 48.00mmol) solution cooled to -30 C, in -30 C under, 0.5 hours slowly dropping WD2 (2.27g, 12 . 35mmol) of THF (30 ml) solution to the reaction mixture. The reaction liquid heating to room temperature reaction 16 hours, adding water quenching reaction, mixed solution under vacuum to evaporate to dry, adding water and ethyl acetate, to obtain white solid to settle out, filtering to obtain solid, shall WD1 (1.19g). The aqueous phase is further extracted with ethyl acetate, the combined organic layer was dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to get the crude product, the crude product of ethyl acetate and hexane processing, filtering to obtain WD1.

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

Introduction of a new synthetic route about Ethyl quinuclidine-4-carboxylate

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).

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
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Extracurricular laboratory: Synthetic route of 40117-63-3

40117-63-3, 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. Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3,the quinuclidine compound, it is a common compound, a new synthetic route is introduced below.

To a stirred suspension of quinuclidine-4-carboxylic acid hydrochloride (5.5 g) in 30 mL of dry THF at 0 C. was added borane dimethyl sulfide complex (6.7 g, 3 eq.). The reaction mixture was stirred at room temperature for 1 hr and heated to reflux for 16 hr. It was then quenched with drop-wise addition of methanol (7 mL) at 0 C. The solvent was then removed under reduced pressure, and the crude product obtained was purified by column chromatography (Silica gel, 20% EA:Hexane) to afford the product quinuclidin-4-ylmethanol N-borane complex as a white solid (1.35 g, 30%).

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

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1-azabicyclo[2.2.2]oct-4-yl{bis[4-(methyloxy)phenyl]}methanol A solution of 4-(methyloxy)phenylmagnesiumbromide (0.5 M in THF, 6.5 mL, 3.25 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1587 g, 0.866 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 (0.273 g, 89.0%). EI-MS m/z 354(M+H+) Rt (1.74 min).

New learning discoveries about 22766-68-3

22766-68-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22766-68-3 ,Ethyl quinuclidine-4-carboxylate, other downstream synthetic routes, hurry up and to see

Name is Ethyl quinuclidine-4-carboxylate, as a common heterocyclic compound, it belongs to quinuclidine compound, and cas is 22766-68-3, its synthesis route is as follows.

1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane/30 ether, 20.0 mL, 32 mmol) was chilled down to -30 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (1.51 g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at -30 C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with H2O and then evaporated to dryness under vacuum. H2O and EtOAc were added, causing a white solid to crash out. This solid was filtered off, to give the title compound (0.79 g). The aqueous phase was further extracted with EtOAc, the combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The crude product was treated with EtOAc and hexane and filtered to yield more of the title compound (0.67 g). Total yield (1.46 g, 60.7%). EI-MS m/z 294(M+H+) Rt (1.37 min).

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Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.

1 Azabicyclo 2.2.2Joct-4 yl(diphe yl)methanol ;A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane / 30 ether, 20.0 mL, 32 mmol) was chilled down to -30 C under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4- carboxylate (1.51g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at -30 C over 25 min. The reaction was allowed to warm up to room temperature overnight. The reaction was quenched with H20 and then evaporated to dryness under vacuum. H20 and EtOAc were added, causing a white solid to crash out. This solid was filtered off, to give the title compound (0.79 g). The aqueous phase was further extracted with EtOAc, the combined organic layers were dried over MgS04, filtered, and concentrated under vacuum. The crude product was treated with EtOAc and hexane and filtered to yield more of the title compound (0.67 g). Total yield (1.46 g, 60.7%). EI-MS m/z 294 (M+H+) Rt (1.37 min).

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/112644; (2005); A2;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

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The chemical industry reduces the impact on the environment during synthesis,40117-63-3,Quinuclidine-4-carboxylic acid hydrochloride,I believe this compound will play a more active role in future production and life.

(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.

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

The important role of Ethyl quinuclidine-4-carboxylate

The chemical industry reduces the impact on the environment during synthesis,22766-68-3,Ethyl quinuclidine-4-carboxylate,I believe this compound will play a more active role in future production and life.

Example 32 Preparation of 1-butyl-4-[hydroxy(di-3-thienyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide A solution of n-Butyl lithium (2.5M in hexanes, 5.0 mL, 12.5 mmol) was chilled to -78 C. under Ar. 3-Bromothiophene (1.15 mL, 12.3 mmol) dissolved in ethyl ether (4.0 mL) was slowly added to the reaction mixture. The reaction was stirred for 30 min and then ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.7640 g, 4.16 mmol) in THF/Et2O (4 mL/4 mL) was added. The reaction was allowed to warm up from -78 C. to room temperature over 16 h then slowly quenched with water. The reaction was concentrated and the resulting brown solid was taken up in water and DCM. The organic phase was separated, dried over MgSO4, filtered and concentrated under vacuum to give a brown solid. The solid was dissolved in DMSO and purified by preparatory HPLC to give the title compound (0.1736 g, 9.4%). EI-MS m/z 362(M+) Rt (1.73 min).

Analyzing the synthesis route of 22766-68-3

1-azabicyclo[2.2.2]oct-4-yl[bis(3-methylphenyl)]methanol A solution of 3-methylphenylmagnesiumbromide (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 (0.1484 g, 0.810 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 (0.1806 g, 69.4%). EI-MS m/z 322(M+H+) Rt (1.54 min).