Heterocyclic Building Blocks-Quinuclidine

One of the major reasons is to use measurements of the macroscopic properties of a system, the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 22766-68-3, introduce a new downstream synthesis route., 22766-68-322766-68-3

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)., 22766-68-3

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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

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 40117-63-340117-63-3, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 40117-63-3, name is Quinuclidine-4-carboxylic acid hydrochloride. A new synthetic method of this compound is introduced below.

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).

A chemical reaction often occurs in steps, although it may not always be obvious to an observer. Thank you very much for taking the time to read this article. If you are also interested in other aspects of Quinuclidine-4-carboxylic acid hydrochloride,, you can also browse my other articles. Thank you very much for taking the time to read this article.

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

A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place., 22766-68-3. The reaction mechanism is the process, or pathway, by which a reaction occurs.22766-68-3. An updated downstream synthesis route of 22766-68-3 as follows.

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 molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of Ethyl quinuclidine-4-carboxylate, , We look forward to the emergence of more reaction modes in the future.

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

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 22766-68-322766-68-3, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 22766-68-3, name is Ethyl quinuclidine-4-carboxylate. A new synthetic method of this compound is introduced below.

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%.

A chemical reaction often occurs in steps, although it may not always be obvious to an observer. Thank you very much for taking the time to read this article. If you are also interested in other aspects of Ethyl quinuclidine-4-carboxylate,, you can also browse my other articles. Thank you very much for taking the time to read this article.

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

A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place., 40117-63-3. The reaction mechanism is the process, or pathway, by which a reaction occurs.40117-63-3. An updated downstream synthesis route of 40117-63-3 as follows.

Step 4. Quinuclidin-4-ylcarbonyl chloride hydrochloride Quinuclidine-4-carboxylic acid hydrochloride (0.192 g, 0.001 mole) was suspended in dichloromethane (5 ml) and dimethylformamide (1 drop) and oxalyl chloride (0.436 ml. 0.635 g, 0.005 mole) were added. The resulting suspension was heated to reflux under an atmosphere of argon for six hours. Following concentration of the suspension in vacuo the residue was suspended in dichloromethane, concentrated in vacuo and finally dried in vacuo to give the title compound as a pale brown solid.

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of Quinuclidine-4-carboxylic acid hydrochloride, , We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; SmithKline Beecham p.l.c.; US6281226; (2001); B1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place., 22766-68-3. The reaction mechanism is the process, or pathway, by which a reaction occurs.22766-68-3. An updated downstream synthesis route of 22766-68-3 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).

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of Ethyl quinuclidine-4-carboxylate, , We look forward to the emergence of more reaction modes in the future.

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

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 22766-68-322766-68-3, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 22766-68-3, name is Ethyl quinuclidine-4-carboxylate. A new synthetic method of this compound is introduced below.

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)., 22766-68-3

A chemical reaction often occurs in steps, although it may not always be obvious to an observer. Thank you very much for taking the time to read this article. If you are also interested in other aspects of Ethyl quinuclidine-4-carboxylate,, you can also browse my other articles. Thank you very much for taking the time to read this article.

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

40117-63-3, One of the major reasons is to use measurements of the macroscopic properties of a system, the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 40117-63-3, introduce a new downstream synthesis route.

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:

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of Quinuclidine-4-carboxylic acid hydrochloride, , We look forward to the emergence of more reaction modes in the future.

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

22766-68-3, One of the major reasons is to use measurements of the macroscopic properties of a system, the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 22766-68-3, introduce a new downstream synthesis route.

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.

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of Ethyl quinuclidine-4-carboxylate, , We look forward to the emergence of more reaction modes in the future.

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

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 40117-63-340117-63-3, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 40117-63-3, name is Quinuclidine-4-carboxylic acid hydrochloride. A new synthetic method of this compound is introduced below.

Example 1(Quinuclidin-4-yl)methanol (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.

Thank you very much for taking the time to read this article. If you are also interested in other aspects of Quinuclidine-4-carboxylic acid hydrochloride, , you can also browse my other articles.

Reference£º
Patent; CoMentis, Inc.; US2009/88418; (2009); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider