Month: August 2020

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

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.

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

Reference£º
Patent; Chiesi Farmaceutici S.p.A.; US2012/276018; (2012); 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

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

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

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).

With 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

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

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).

With 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

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 5: (S)-4-((1-(5-(6-methoxynaphthalen-2-yl)-JH-imidazol-3-ium-2-yl)- 7-(methylamino)- 7-oxoheptyl)carbamoyl)quinuclidin-1-ium mono L-tartrate salt (E5) A solution of 4-carboxyquinuclidin-1-ium chlorhydrate (1.3 eq.) in DMF (0.2 M) was treated with TBTU (1.3 eq.) and NMM (2.6 eq.). The reaction mixture was stirred at room temperature for 10 mm and then added to a solution of E4 in DMF (0.2 M). The reaction was stirred at RT for 2 h, then filtered and purified by RP-HPLC (CH3CN/H20 + 0.1 % TFA). The product was obtained as TFA salt which was partitioned between EtOAc and sat. aq. NaHCO3. The organicphase was separated, dried (Na2504) and concentrated under reduced pressure. The resulting pale yellow 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. (400 MHz, 300K, DMSOd 6) oe: 11.5 (br s, 1H), 8.14 (br s, 1H), 7.95-7.73 (m, 4H), 7.66 (m, 1H), 7.54 (m, 1H), 7.27 (d, 1H, J2 Hz), 7.12 (dd, 1H, J8.8 and 2.4 Hz), 4.99 (m, 1H), 3.89 (s, 2H), 3.86 (s, 3H), 3.16 (m,6H), 2.54 (d, J4.4 Hz), 3H), 2.02 (t, 2H, J7.4 Hz), 2.01 (m, 6H), 1.83 (m, 2H), 1.48 (m, 2H),1.35-1.15 (m, 4H). MS (ESj C30H39N503: 518 (M+H).

With 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

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

With the rapid development of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

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

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

Ethyl quinuclidine-4-carboxylate (900 mg, 4.91 mmol) was hydrolyzed in a mixture of ethanol (2 mL) and sodium hydroxide (aq) (2M, 7.5 mL) at 50 C. The reaction was followed by TLC (methanol/diethylamine 20/1). After 3 hours the mixture was neutralized with HC1 (2 M) to pH=5 and evaporated. The residue was extracted with methanol which however also extracted NaCl. The extract was evaporated and the solid was extracted with ethanol which was not very effective in extracting the desired zwitterionic amino acid. All extracts and solids were combined and HC1 (2 M) was added to pH< 1 and the mixture was evaporated until it was completely dry. The solid residue was suspended in dichioromethane (10 mL) and oxalyl chloride (25 mmol, 2.3 mL) was added followed by two drops of N,N-dimethylformamide. The mixture was refluxed for 6 hours and then evaporated to dryness. To the residue was added N,N-dimethylformamide (10 mL) and sodium azide (10.4 mmol, 680 mg) and the mixture was stirred at 50 C for 20 h, then partitioned between saturated sodium carbonate and toluene. A three phase liquid system was formed. The toluene phase (on top) was collected, dried, and heated at reflux for 1 hours (visible gas formation occurred before reaching the reflux temperature), then cooled and extracted three times with HC1 (SM, 3 x 20 mL). The aqueous phases were combined and heated at reflux for 1 h, then evaporated to almost dryness and triturated with abs. ethanol. The precipitate was collected and gave the desired 4-aminoquinuclidine as the dihydrochloride (173 mg, 0.87 mmol, 18% yield). ?H NMR (400 MHz, deuterium oxide) 3.68- 3.52 (m, 4H), 2.37-2.23 (m, 4H). With the rapid development of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate Reference£º
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; WAHLSTROeM, Larisa, Yudina; VON WACHENFELDT, Henrik; BERGNER, Magnus, Gustav Wilhelm; DREISCH, Klaus; POPOV, Kyrylo; KOVALENKO, Oleksnadr; KLINGSTEDT, Per Tomas; (357 pag.)WO2019/40106; (2019); A2;,
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(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).

With the rapid development 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

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

A solution of phenyllithium (1 .9 M in 70 cyclohexane/30 ether, 22.30 mL, 42.40 mmol) was cooled down to -30C under nitrogen. A solution of ethyl 1 -azabicyclo[2.2.2]octane-4-carboxylate (III, 2.0 g, 10.90 mmol) in THF (27.0 mL) was slowly added to the reaction mixture at -30C over 25 mins. The reaction mixture was allowed to warm up to room temperature over 16h. The reaction was quenched with water (10.0 mL) and then evaporated to dryness under vacuum. Water (40.0 mL) and ethyl acetate (40.0 mL) were added, causing a white solid to crash out. This solid was filtered off under vacuum, to give a white powder (2.46 g, 76.8%). 1 -azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV): ^H-NMR (300 MHz, CDC ) delta 7.54 – 7.51 (m, 3H), 7.33 – 7.20 (m, 6H), 2.85 – 2.80 (m, 6H), 1 .78 – 1.72 (m, 6H). MS (ESI) m/z calcd for C20H23NO: 293, found 294 [M + H]+.

With the rapid development of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

Reference£º
Patent; HOVIONE SCIENTIA LIMITED; TURNER, Craig; LOURENCO, Nuno Torres; SOBRAL, Luis; ANTUNES, Rafael; SANTOS, Maria; ESPADINHA, Margarida; (35 pag.)WO2018/87561; (2018); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider