Day: September 1, 2020

(S)-(1-Ethylpyrrolidin-2-yl)methanamine, cas is 22795-99-9, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,22795-99-9

Example 43 Synthesis of N2-cyclohexylmethyl-N4-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-N6-(3-fluoro-4-methoxphenyl)-1,3,5-triazine-2,4,6-triamine (141) To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of N,N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp 68-69¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 8.2 min, 97.1percent purity; MS (ESI): m/z 458 (M+H, 100), 362 (2.8), 230 (85.4).

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Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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Benzo-18-crown 6-Ether, cas is 14098-24-9, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,14098-24-9

General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

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Reference£º
Article; Zielinski, Matthew E.; Tracy, Adam F.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1701 – 1704;,
Chiral Catalysts
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22795-99-9, (S)-(1-Ethylpyrrolidin-2-yl)methanamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In a clean and dry Tiny-clave reactor covered with aluminum foil, 1-iodo-m-carborane (0.09 mmol), amine (0.135 mmol), base (0.27 mmol) and ligand (4 molpercent with respect to carborane) were solved in degassed dry THF (1 mL). The catalyst (2 molpercent with respect to carborane) was added and the solution was degassed one more time. The reactor was closed and filled with the required pressure of CO, placed in a pre heated oil bath and heated at 85?C. Progress of the reaction was monitored by GC-MS analysis. After finishing the reaction, the oil bath was removed, cooled to room temperature and the CO was flushed with nitrogen. The reaction mixture was filtered through a celite bed. The celite was washed with ethyl acetate and the collected filtrates were concentrated and purified by column chromatography. Conditions were as follows:Compound 1: chloroform/ethanol 75/25; Compound 2: chloroform/ethanol 95/05; Compound 3: chloroform/ethanol 92/08; Compound 4: chloroform/ethanol 92/08, 22795-99-9

As the paragraph descriping shows that 22795-99-9 is playing an increasingly important role.

Reference£º
Article; Gona, Kiran Babu; Go?mez-Vallejo, Vanessa; Llop, Jordi; Tetrahedron Letters; vol. 54; 8; (2013); p. 941 – 944;,
Chiral Catalysts
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1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, cas is 250285-32-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,250285-32-6

A microwave -vial was loaded with NHC HCl (0.55 mmol), palladium(II) chloride (89 mg, 0.50 mmol), potassium carbonate (345 mg, 2.5 mmol), 3-chloropyridine (2 mL) and a magnetic bar. The mixture was heated in a microwave reactor for 45 min at 200 C. The mixture was diluted with methylene chloride, filtered over a plug of silica gel that was covered with celite and the silica gel was rinsed with methylene chloride. The solvent and excess chloropyridine were removed in vacuo, the product was triturated in pentane and the pentane was decanted. Drying in vacuo afforded the desired products as yellow solids.(IPr)PdCl2(3-chloropyridine):309 mg (88 %) of the title compound were obtained using IPr-HCl (234 mg, 0.550 mmol). 1H NMR (300 MHz, CDCI3): delta (ppm) = 8.60 (d, 3J= 2.4 Hz, 1H), 8.52 (dd, 3J = 5.5 Hz, 3J= 1.3 Hz, 1H), 7.55 (ddd, 3J= 8.2 Hz, 3J= 2.3 Hz, 3J= 1.3 Hz, 1H), 7.50 (t, 3J = 7.8 Hz, 2H), 7.35 (d, 3J= 7.7 Hz, 4H), 7.14 (s, 2H), 7.07 (dd, 3J= 8.2 Hz, 3J= 5.5 Hz), 3.16 (sept, 3J= 6.7 Hz, 4H), 1.48 (d, 3J= 6.6 Hz, 12H), 1.12 (d, 3J= 6.9 Hz, 12H).

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Reference£º
Patent; UNIVERSITY OF HAWAII; NAVARRO, Oscar; WINKELMANN, Ole, H.; WO2011/71881; (2011); A2;,
Chiral Catalysts
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(R)-2′-amino-[1,1′-binaphthalen]-2-ol, cas is 137848-28-3, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,137848-28-3

General procedure: To a mixture of 3,4-dimethoxy-3-cyclobutene-1 ,2-dione (Ia) (0.2 mmol) in MeOH (0.25- 1 mL) the amine 2a-m was firstly added at room temperature. After the correspondingreaction time (ti) (see Table I), the amine 4a-n (0.2 mmol) was then added with MeOH (1.75-1 mL). After the corresponding reaction time (t2) (see Table I and Table Ibis), the product was purified by filtration or by column chromatography. Yields are reported in Table I and Table Ibis and pure compounds were obtained as stable solids.

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Reference£º
Patent; UNIVERSIDAD DE ZARAGOZA; CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC); MARQUEZ LOPEZ, Maria Eugenia; ALEGRE REQUENA, Juan Vicente; PEREZ HERRERA, Raquel; (70 pag.)WO2016/5407; (2016); A1;,
Chiral Catalysts
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1,4,7,10,13-Pentaoxacyclopentadecane, cas is 33100-27-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,33100-27-5

EXAMPLE 1 A mixture of 1-[3-(naphth-2-ylmethoxy)phenyl]cyclohexanol (0.65 g), sodium hydride (0.096 g of a 50percent w/w dispersion in mineral oil), 1,4,7,10,13-pentaoxacyclopentadecane (hereinafter 15-crown-5, (0.06 g) and tetrahydrofuran (10 ml) was stirred at ambient temperature for 15 minutes. methyl iodide (0.12 ml) was added and the mixture was stirred at ambient temperature for 15 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, dried (MgSO4 and evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained 1-methoxy-1-[3-(naphth-2-ylmethoxy)phenyl]cyclohexane (0.35 g, 54percent), m.p. 74-75¡ãC. The 1-[3-(naphth-2-ylmethoxy)phenyl]cyclohexanol starting material was obtained as follows:-.

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Reference£º
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; ICI-PHARMA; EP375452; (1994); B1;,
Chiral Catalysts
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(S)-2-(Methoxymethyl)pyrrolidine, cas is 63126-47-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,63126-47-6

Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20¡ã C. To this was added DIEA (11.5 mL, 60 mmol) followed by 3-fluoro-4-methoxyaninline (8.47 g, 60 mmol) in 20 mL CH3CN (reaction froze). The reaction was allowed to warm to room temperature after about 1 hour at -20¡ã C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0¡ã C. before adding DIEA (11.5 mL, 66 mmol). 2-Aminomethyl-1-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) and S-(+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20 mL 1,4-dioxane were added. The reaction was heated at about 50¡ã C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH3OH:ethyl acetate. The material collected from the column was then dissolved in water and extracted in CH2Cl2 (4 times), dried over MgSO4, and concentrated to dryness to give a brown solid 145 (9.7 g, 27.6percent yield), 71-72¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 5.37 min, 90.3percent purity; 1H NMR (600 MHz, CDC3, 55¡ã C.) delta 7.69 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.86 (t, J=9 Hz, 1H), 4.29 (s, 1H), 3.90-3.96 (m, 1H), 3.84 (s, 3H), 3.63-3.81 (m, 6H), 3.35 (s, 3H), 3.23-3.25 (m, 1H), 2.85 (broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2.04 (m, 6H), 1.37 (apparent t, J=7.2 Hz, 3H); 13C NMR (150.8 MHz, CDCl3, 55¡ã C.) delta 165.8, 163.8 (2C), 152.3 (d, Jc-f=243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108.9, rotamer or diastereomer), 72.8, 66.6, 59.0, 57.0, 56.6, 53.7, 51.0, 46.8, 42.2, 28.4 (28.2, rotamer or diastereomer), 23.1 (23.0, rotamer or diastereomer), 10.9; MS (ESI) mn/z 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).

With the rapid development of chemical substances, we look forward to future research findings about 63126-47-6

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
Chiral Catalysts
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6,6′-((1E,1’E)-((2,3-Dimethylbutane-2,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2,4-di-tert-butylphenol), cas is 351498-10-7, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,351498-10-7

In a nitrogen atmosphere, add to the reactor,2,2 ‘-[(1,1,2,2-tetramethyl-1,2-ethylenediyl) bis (nitromethyl)] bis [4,6-bis (1,1-dimethyl (Ethyl)] phenol, 16.46g (30mmol),21.6 g (152 mmol) of boron trifluoride-ether complex,300ml toluene20 g (152 mmol) of N, N-diisopropylethylamine was stirred with heating at 40 C for 2.5 hours.Cool to room temperature, add 300ml of water, and separate the filtrate into organic and aqueous layers.The organic layer was washed twice with a saturated sodium carbonate aqueous solution and dried over magnesium sulfate.The obtained solid was recrystallized from toluene (150 ml) and ethanol (750 ml),This gave 18.78 g of crude product. The crude product is under pressure 3 ¡Á 10-3Pa,Sublimation at a temperature of 225 C gave compound [69] (light yellow solid).

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Reference£º
Patent; TORAY ADVANCED MATERIALS RESEARCH LABORATORIES (CHINA) CO., LTD.; WAN, PENG; JIN, GUANGNAN; IKEDA, TAKESHI; LI, JINCAI; TANAKA, DAISAKU; (48 pag.)TW2019/25212; (2019); A;,
Chiral Catalysts
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1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, cas is 250285-32-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,250285-32-6

General procedure: Under an N2 atmosphere, the mixture of imidazolium salts 1 (1.1 mmol), benzoxazole or benzothiazole (2.0 mmol), PdCl2 (1.0 mmol) and K2CO3 (1.1 mmol) was stirred in anhydrous THF (10 mL) under reflux for 16 h. After cooling, filtration and evaporation,the residue was purified by preparative TLC on silica gelplates eluting with CH2Cl2 to afford the corresponding N-heterocyclic carbene-palladium(II) complexes 3a-d.

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Reference£º
Article; Wang, Tao; Xie, Huanping; Liu, Lantao; Zhao, Wen-Xian; Journal of Organometallic Chemistry; vol. 804; (2016); p. 73 – 79;,
Chiral Catalysts
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63126-47-6, (S)-2-(Methoxymethyl)pyrrolidine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,63126-47-6

Step 2: (S)-ferf-Butyl 2-(4-((2-(methoxymethyl)pyrrolidin-l-yl)methyl)benzamido)-4-(thiophen- 2-yl)phenylcarbamate (75); [0708] To a solution of chloride 74 (0.30 g, 0.68 mmol) in DCM (7 mL) was added (S)-2- (methoxymethyl)pyrrolidine (86 mg, 0.75 mmol), K2CO3 (0.31 g, 2.24 mmol) and NaI (12 mg, 0.075 mmol). Acetone (3 mL) was added and the reaction mixture was heated to reflux for 3 days then concentrated. The residue was taken up in AcOEt, washed with H2O, brine, dried overMgSO4, filtered and concentrated to give title compound 75 (0.323 g, 91percent yield).[0709] 1H NMR (DMSO-de) delta (ppm): 9.87 (s, IH), 8.72 (s, IH), 7.91 (d, J= 8.4 Hz, 2H),7.80 (d, J= 2.2 Hz, IH), 7.59 (d, J= 8.6 Hz, IH), 7.51 (dd, J= 4.9, 1.0 Hz, IH), 7.49 (dd, J= 8.4,2.3 Hz, IH), 7.45 (d, J= 8.6 Hz, 2H), 7.44 (dd, J= 3.7, 1.0 Hz, IH), 7.11 (dd, J= 12.5 Hz, IH),3.39 (q, J= 5.7 Hz, IH), 2.79 to 2.75 (m, IH), 2.73 to 2.67 (m, IH), 2.15 (q, J= 7.6 Hz, IH), 1.86(dq, J= 11.9, 7.8 Hz, IH), 1.66 to 1.58 (m, IH), 1.54 to 1.46 (m, IH), 1.44 (s, 9H).

As the paragraph descriping shows that 63126-47-6 is playing an increasingly important role.

Reference£º
Patent; METHYLGENE INC.; WO2007/118137; (2007); A1;,
Chiral Catalysts
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