Downstream synthetic route of Ethyl quinuclidine-4-carboxylate

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO60,mainly used in chemical industry, its synthesis route is as follows.

1-azabicyclo[2.2.2]oct-4-yl]bis(4-fluorophenyl)]methanol A solution of 4-fluorophenylmagnesiumbromide (1.0 M in THF, 4.4 mL, 4.4 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1973 g, 1.08 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 (0.3152 g, 88.9%). EI-MS m/z 330(M+H+) Rt (1.65 min).

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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

Application of 6-Bromobenzo[d]oxazol-2(3H)-one

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

A common heterocyclic compound, the quinuclidine compound, name is Ethyl quinuclidine-4-carboxylate,cas is 22766-68-3, mainly used in chemical industry, its synthesis route is as follows.

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).

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

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

Application of 2-(4-((2,4-Dioxothiazolidin-5-yl)methyl)phenoxy)acetic acid

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

A common heterocyclic compound, the quinuclidine compound, name is Ethyl quinuclidine-4-carboxylate,cas is 22766-68-3, mainly used in chemical industry, its synthesis route is as follows.

Crude preparation: azabicyclo [2.2.2] octane-4-carboxylic acid ethyl ester (18.3g, 0 . 10mol) dissolved in 3L tetrahydrofuran, under the protection of nitrogen, the solution is cooled down 5-15C, dropwise 0.30mol phenyl magnesium bromide. 5-15 C preserving heat and stirring 1 hour later (sampling TLC monitoring reaction progress). Add 10 ml water quenching. The liquid, aqueous phase using 100 ml tetrahydrofuran extraction two, combined with the phase water washing, drying and filtering. Removing part of the solvent under reduced pressure, the rest about 50 ml, residues 20 C stirring sleepovers crystallization. Filtering, washing (petroleum ether 2¡Á20 ml), the filtration cake at 40 C vacuum drying, be yellowish crystal 13.80g, yield 47.1%.Refining wuhu bromine ammonium : crude 100g dissolved in 80 C of 320 ml water-acetone 640 ml mixture, and 5g activated carbon decolourizations, filtering. Filtrate lower the temperature to 25 C, thermal insulation 1 hour. 1-2 hours to lower the temperature to 0-5 C and thermal insulation 3 hours. Filtering, the filter cake is washed with frozen 1:2 acetone-water washing two times (2x20ml). The filtration cake at 60 C vacuum drying, getting white crystalline solid (92g, yield 92%). (Normalization HPLC) purity of 99.25%.

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

Reference£º
Patent; Anhui Dexinjia Biopharm Co., Ltd.; Li, Xuekun; Xu, Kun; (5 pag.)CN105461710; (2016); A;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Analyzing the synthesis route of 22766-68-3

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,Molecular formula: C10H17NO2,mainly used in chemical industry, its synthesis route is as follows.

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).

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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

Analyzing the synthesis route of 22766-68-3

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,Molecular formula: C10H17NO2,mainly used in chemical industry, its synthesis route is as follows.

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).

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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

Share a compound : Ethyl quinuclidine-4-carboxylate

Big data shows that 22766-68-3 is playing an increasingly important role.

Ethyl quinuclidine-4-carboxylate,22766-68-3,belong quinuclidine compound,the synthetic route is as follows.

Example 33 Preparation of 1-azabicyclo[2.2.2]oct-4-yl(di-3-thienyl)methanol A solution of t-Butyl lithium (1.7M in pentanes, 5.8 mL, 9.86 mmol) was chilled to -78 C. under Ar. 3-Bromothiophene (0.46 mL, 4.90 mmol) dissolved in THF (4.0 mL) was slowly added to the reaction mixture over 6 min. The reaction was stirred for 30 min and then ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.3132 g, 1.71 mmol) in THF (4 mL) was added. The reaction was allowed to warm up from -78 C. to room temperature over 16 h. After 14 hours, the reaction was slowly quenched with water. EtOAc was added, causing a grey solid to crash out. The solid was filtered off to give the title compound (0.3375 g, 64.6%). EI-MS m/z 306(M+H)+ Rt (1.27 min).

Big data shows that 22766-68-3 is playing an increasingly important role.

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

Analyzing the synthesis route of Ethyl quinuclidine-4-carboxylate

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,Molecular formula: C10H17NO2,mainly used in chemical industry, its synthesis route is as follows.

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.

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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

Downstream synthetic route of Ethyl quinuclidine-4-carboxylate

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,Molecular formula: C10H17NO2,mainly used in chemical industry, its synthesis route is as follows.

1-azabicyclo[2.2.2]oct-4-yl(di-2-naphthalenyl)methanol A solution of (2-naphthalenyl)magnesiumbromide (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 (0.1597 g, 0.871 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 (0.265 g, 77.3%). EI-MS m/z 394(M+H+) Rt (1.90 min).

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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

Some tips on Ethyl quinuclidine-4-carboxylate

With the complex challenges of chemical substances, we look forward to future research findings about 22766-68-3,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,mainly used in chemical industry, its synthesis route is as follows.

1-azabicyclo[2.2.2]oct-4-yl[bis(4-methylphenyl)]methanol A solution of 4-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 (0.1509 g, 0.823 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 (0.2291 g, 86.6%). EI-MS m/z 322(M+H+) Rt (1.57 min).

With the complex challenges of chemical substances, we look forward to future research findings about 22766-68-3,belong quinuclidine compound

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

Downstream synthetic route of Ethyl quinuclidine-4-carboxylate

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

As a common heterocyclic compound, it belong quinuclidine compound,Ethyl quinuclidine-4-carboxylate,22766-68-3,Molecular formula: C10H17NO2,mainly used in chemical industry, 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).

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate,belong quinuclidine compound

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