Category: quinuclidine

22766-68-3 A common heterocyclic compound, 22766-68-3,Ethyl quinuclidine-4-carboxylate, 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.

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).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22766-68-3,Ethyl quinuclidine-4-carboxylate,its application will become more common.

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

A common heterocyclic compound, 22766-68-3,Ethyl quinuclidine-4-carboxylate, 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., 22766-68-3

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22766-68-3,Ethyl quinuclidine-4-carboxylate,its application will become more common.

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

A common heterocyclic compound, 22766-68-3,Ethyl quinuclidine-4-carboxylate, 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[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).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22766-68-3,Ethyl quinuclidine-4-carboxylate,its application will become more common.

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

A common heterocyclic compound, 22766-68-3,Ethyl quinuclidine-4-carboxylate, 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).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Ethyl quinuclidine-4-carboxylate,22766-68-3,its application will become more common.

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

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

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).

22766-68-3 is used more and more widely, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

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

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

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

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

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.,40117-63-3

Step 8: (S)-4- ((1- (5- (2-methoxyquinolin-1-ium-3-yl)oxazol-2-yl)- 7- (methylamino)- 7-oxoheptyl)carbamoyl)quinuclidin-1-ium mono L-tartrate salt (F8)A solution of 4-carboxyquinuclidin-1-ium chlorhydrate (1.3 eq.) in DMF (0.1 M) was treated with HOBt (1.3 eq.), EDC HC1 (1.3 eq.) and DIPEA (1.3 eq.). The reaction mixture was stirred at room temperature for 10 minutes and then added to F7. The reaction was stirred for at RT for 48 h, filtered and directly purified by RP-HPLC (Acetonitrile/H20 + 0.1 % TFA). The product was obtained as TFA salt which was partitioned between DCM and sat. aq. NaHCO3. Theorganic phase was separated dried over Na2504 and concentrated under reduced pressure. The resulting solid was dissolved in acetonitrile/H20 (1:1) and treated with L-tartaric acid (1 eq.). The resulting solution was lyophilized to obtain the title compound. MS (ESj C29H37N504: 520 (M+H).

With the complex challenges of chemical substances, we look forward to future research findings about Quinuclidine-4-carboxylic acid hydrochloride

Reference£º
Patent; IRBM SCIENCE PARK S.P.A.; C.N.C.C.S. SCARL COLLEZIONE NAZIONALE DEI COMPOSTI CHIMICI E CENTRO SCREENING; ALTAMURA, Sergio; BIANCOFIORE, Ilaria; BRESCIANI, Alberto; FERRIGNO, Federica; HARPER, Steven; LAUFER, Ralph; ONTORIA ONTORIA, Jesus Maria; MALANCONA, Savina; MONTEAGUDO, Edith; NIZI, Emanuela; ORSALE, Maria Vittoria; PONZI, Simona; PAONESSA, Giacomo; SUMMA, Vincenzo; VENEZIANO, Maria; WO2014/67985; (2014); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Name is Quinuclidine-4-carbonitrile, as a common heterocyclic compound, it belongs to quinuclidine compound, and cas is 26458-78-6, its synthesis route is as follows.,26458-78-6

Quinuclidine-4-carbonitrile (4 g, 29.4 mmol) was treated with 30 mL of 6 N aqueous HCl solution and stirred under reflux for 16 hr. The reaction mixture was cooled and evaporated to dryness under reduced pressure. The solid obtained was triturated with 20% ether-hexane to afford the HCl salt of quinuclidine-4-carboxylic acid (5.5 g, quantitative).

With the complex challenges of chemical substances, we look forward to future research findings about Quinuclidine-4-carbonitrile

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

Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,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 is used more and more widely, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

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

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

Step 8: (S)-4- ((1- (5- (2-methoxyquinolin-1-ium-3-yl)oxazol-2-yl)- 7- (methylamino)- 7-oxoheptyl)carbamoyl)quinuclidin-1-ium mono L-tartrate salt (F8)A solution of 4-carboxyquinuclidin-1-ium chlorhydrate (1.3 eq.) in DMF (0.1 M) was treated with HOBt (1.3 eq.), EDC HC1 (1.3 eq.) and DIPEA (1.3 eq.). The reaction mixture was stirred at room temperature for 10 minutes and then added to F7. The reaction was stirred for at RT for 48 h, filtered and directly purified by RP-HPLC (Acetonitrile/H20 + 0.1 % TFA). The product was obtained as TFA salt which was partitioned between DCM and sat. aq. NaHCO3. Theorganic phase was separated dried over Na2504 and concentrated under reduced pressure. The resulting solid was dissolved in acetonitrile/H20 (1:1) and treated with L-tartaric acid (1 eq.). The resulting solution was lyophilized to obtain the title compound. MS (ESj C29H37N504: 520 (M+H).

As the rapid development of chemical substances, we look forward to future research findings about 40117-63-3

Reference£º
Patent; IRBM SCIENCE PARK S.P.A.; C.N.C.C.S. SCARL COLLEZIONE NAZIONALE DEI COMPOSTI CHIMICI E CENTRO SCREENING; ALTAMURA, Sergio; BIANCOFIORE, Ilaria; BRESCIANI, Alberto; FERRIGNO, Federica; HARPER, Steven; LAUFER, Ralph; ONTORIA ONTORIA, Jesus Maria; MALANCONA, Savina; MONTEAGUDO, Edith; NIZI, Emanuela; ORSALE, Maria Vittoria; PONZI, Simona; PAONESSA, Giacomo; SUMMA, Vincenzo; VENEZIANO, Maria; WO2014/67985; (2014); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider