Day: November 20, 2020

As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-2-(Methoxymethyl)pyrrolidine,63126-47-6,Molecular formula: C6H13NO,mainly used in chemical industry, 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, CDCl3, 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) m/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 synthetic route has been constantly updated, we look forward to future research findings about (S)-2-(Methoxymethyl)pyrrolidine,belong chiral-catalyst compound

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is 1,3-Dimesityl-1H-imidazol-3-ium chloride, and cas is 141556-45-8, its synthesis route is as follows.,141556-45-8

General procedure: A 20 mL vial was charged with the NHC¡¤HCl (300 mg, 1 equiv.) and the zinc salt (1 equiv.). Tetrahydrofuran (5 mL) was added, the vial was sealed with a screw-cap and the reaction was stirred at 60C for two hours. The mixture was allowed to reach room temperature and the solvent was removed under reduced pressure toafford the desired product.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride

Reference£º
Article; Santoro, Orlando; Nahra, Fady; Cordes, David B.; Slawin, Alexandra M.Z.; Nolan, Steven P.; Cazin, Catherine S.J.; Journal of Molecular Catalysis A: Chemical; vol. 423; (2016); p. 85 – 91;,
Chiral Catalysts
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-22-8,trans-Cyclohexane-1,2-diamine,as a common compound, the synthetic route is as follows.

General procedure: To a solution of the corresponding sulfonyl chloride (26.0 mmol)in 26 mL of dichloromethane at 0 C, was added rapidly propane-1,3-diamine or (rac)-cyclohexane-1,2-diamine (10 eq., 3 M). Themixturewas allowed to reach roomtemperature andwas stirred during10 h. The crude mixture was filtered and the obtained oil was concentratedunder reduced pressure. Then, 10 mL of ice-water were addedto the concentrated mixture and a solid appeared which was filtrated and washed with cool water and dried under vacuum for 12 h., 1121-22-8

As the paragraph descriping shows that 1121-22-8 is playing an increasingly important role.

Reference£º
Article; Del Solar, Virginia; Quinones-Lombrana, Adolfo; Cabrera, Silvia; Padron, Jose M.; Rios-Luci, Carla; Alvarez-Valdes, Amparo; Navarro-Ranninger, Carmen; Aleman, Jose; Journal of Inorganic Biochemistry; vol. 127; (2013); p. 128 – 140;,
Chiral Catalysts
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Name is 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 173035-10-4, its synthesis route is as follows.,173035-10-4

Example 38 50.0g of 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride was added to a 1000 mL single neck round bottom flask containing a Teflon-coated stirbar. 15.2 g of Lithium tert-butoxide (1.3 mol equivalents of Lithium tert-butoxide to 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride) was added to the 1000 mL flask. 190 mL of anhydrous Hexanes was added to the 1000 mL flask and the flask was capped with a septum and the headspace was purged with argon for 15 minutes with stirring. This mixture was stirred for 2 hours at room temperature. After 2 hours the septum on the 1000 mL flask was replaced with a 250 mL addition funnel. 250 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. After the 250 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask an additional 130 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. The additional 130 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask with stirring. A total of 380 mL of CHCl3 was added dropwise to the 1000 mL flask at room temperature under an atmosphere of argon with stirring. Once the 380 mL of CHCl3 was added to the 1000 1 l flask the additional funnel was removed from the flask and the flask was capped with a septum. The headspace of the flask was purged with argon for 15 minutes. The reaction mixture was stirred for 24 hours under an atmosphere of argon to yield an off-white solution. This off-white solution is cooled to 0 C. and then washed with saturated NH4Cl(aq) (4*200 mL) in a separatory funnel at 22-25 C. The organic layer was then washed with saturated NaCl(aq) (2*200 mL) in a separatory funnel at 22-25 C. The organic layer was then placed in a single neck round bottom flask and the excess chloroform was removed in vacuo to yield the crude product as a powdery off-white solid. The off-white solid was washed with a minimal amount of cold methanol (0 C.) and filtered to give 52.5 g of 1,3-dimesityl-2-(trichloromethyl)imidazolidine (62.1 g theoretical yield) as a white to off-white crystalline powder in 85% yield.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride

Reference£º
Patent; Grubbs, Robert H.; Moore, Jason L.; Morgan, John P.; Bell, Andrew; US2003/83445; (2003); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-(1-Ethylpyrrolidin-2-yl)methanamine,22795-99-9,Molecular formula: C7H16N2,mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

EXAMPLE 2 A mixture of (S)-2-(aminomethyl)-1-ethylpyrrolidine (143 g) and methyl 2-methoxy-5-sulfamoylbenzoate (260 g) in n-butanol (1040 ml) was refluxed for 20 hours, then cooled to room temperature and extracted with a solution of concentrated hydrochloric acid (115 g) in water (1040 ml). The aqueous phase was then alkalinized with concentrated ammonia (about 95 g) and the resulting product was filtered and dried, to obtain 277 g of Levosulpiride (75percent molar yield) that, if desired, can be recrystallized from alcohols such as methanol or ethanol.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine,belong chiral-catalyst compound

Reference£º
Patent; BERTOLINI, Giorgio; BOGOGNA, Luigi; PREGNOLATO, Massimo; TERRENI, Marco; VELARDI, Francesco; US2007/105201; (2007); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, cas is 173035-10-4 its synthesis route is as follows.,173035-10-4

General procedure: [HIPr]2[PdCl4]: 0.45 g (1.0 mmol) of [HIPr]Cl was added to thesolution of 0.14 g (0.48 mmol) PdCl2(cod) in hot CH3CN (5 mL). Themixture was heated for 15 min, until the yellow solution becamered. The solution was cooled to room temperature and solventwas removed under reduced pressure. The product was precip-itated by addition of diethyl ether (2-3 mL). Product yield: 85%;elemental analysis calcd. (%) for PdCl4C54H78N4: C 62.88, H 7.62,N 5.46; found: C 62.37, H 7.46, N 5.40.1H NMR(500 MHz, CD3CN,25C, TMS): = 8.49 (s, 2H, N CH N); 7.57 (t, J(H,H) = 7.8 Hz, 4H,Ar); 7.42 (d, J(H,H) = 7.8 Hz, 8H, Ar); 4.48 (s, 8H, CH2CH2); 3.10(m, J(H,H) = 6.9 Hz, 8H, CH); 1.40 (d, J(H,H) = 6.9 Hz, 24H, CH3); 1.26(d, J(H,H) = 6.9 Hz, 24H, CH3,);13C NMR (125.75 MHz, CD3CN, 25C,TMS): = 160.0 (N CH N); 147.2 (Ar); 131.0 (Ar); 125.5 (Ar); 53.7(CH2CH2); 28.5 (CH); 24.0 (CH3); 23.5 (CH3).

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride

Reference£º
Article; Silarska; Trzeciak; Pernak; Skrzypczak; Applied Catalysis A: General; vol. 466; (2013); p. 216 – 223;,
Chiral Catalysts
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Name is [1,1′-Binaphthalene]-2,2′-diol, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 602-09-5, its synthesis route is as follows.,602-09-5

stirrer, condenser, and a glass reactor equipped with a thermometer, (RS)-1,1′-bi-2-naphthol 32.0 g (0.112 mol), ethylene carbonate 22. 5g (0.256mol), was charged with potassium carbonate 1.6g and toluene 32g, after a heated slurry state up to 110 , and reacted for 10 hours at 110 .A result that was confirmed by HPLC, the remaining amount of 1,1′-bi-2-naphthol was 0.1% or less.After dilution with toluene 416g to the reaction mixture, the organic solvent phase containing the reaction mixture was washed with 10% aqueous sodium hydroxide 48 g, then the wash water was washed with water until neutral.After washing with water, was refluxed dehydrated organic solvent phase, then cooled to room temperature, filtered, the white crystals dried to (RS)-2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene compound obtained (83.3% yield, HPLC purity 99.7%, YI value: 2.8).

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

Reference£º
Patent; TAOKA CHEMICAL COMPANY LIMITED; MATSUURA, TAKASHI; KAWAMURA, MIO; HIRABAYASHI, SHUNICHI; FUJII, KATSUHIRO; (9 pag.)JP6083900; (2017); B2;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO136,mainly used in chemical industry, its synthesis route is as follows.,63126-47-6

1-Tert-Butyl-5- (4-methyl-benzoylamino)-1 H-pyrazolo [3,4-d] thiazole-3- carboxylic acid (50 mg, 0.14 mmoles) was dissolved in 10 ml of anhydrous tetrahydrofuran. Then, 1-hydroxybenzotriazole (23 mg, 0. 168 mmoles) was added followed by addition of N- cyclohexylcarbodiimide N’-methyl polystyrene (155 mg, 0.28 mmoles, loading: 1.8 mmoles/g) and S-2-methoxymethyl pyrrolidine (22 mg, 0.14 mmoles). The mixture was heated at 50¡ãC for overnight. Polymer supported triamine (100 mg, 0.417 mmoles, loading: 4.17 mmoles/g) was added and shaken for 4 hours at 50¡ãC. The resin was filtered off and washed with tetrahydrofuran (2 x 5ml). The filtrate was evaporated in vacuo to give crude product, which was purified by preparative HPLC using MeOH/H2O/TFA solvent system. The combined pure fractions were evaporated in vacuo and further dried on lyophilizer (yield: 36percent, LC: Method A, RT = 4.020 min, MS: M+1 = 456).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-2-(Methoxymethyl)pyrrolidine,belong chiral-catalyst compound

Reference£º
Patent; LEXICON GENETICS, INC; WO2005/95420; (2005); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is (R)-2′-amino-[1,1′-binaphthalen]-2-ol, and cas is 137848-28-3, its synthesis route is as follows.,137848-28-3

General procedure: Modified method [67]. 3-tert-Butylsalicylaldehyde (1.78 g,10.0 mmol) was mixed with (R)-2-amino-2′-hydroxy-1,1′-binaphthyl (2.85 g, 10.0 mmol) in dry toluene (50 mL). A few 4 A molecular sieves were added, and the solution was warmed up to 70 Cand kept for two days at this temperature. The solution was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography (n-hexane/ethyl acetate= 5:1) to give 2H2 as a yellow solid. Yield: 4.09 g (92%). M.p.: 86-88 C. 1H NMR (C6D6): d 13.28 (s, 1H, OH), 8.31 (s, 1H, CHN), 7.80 (m, 4H, aryl), 7.62 (d, J = 8.4 Hz, 1H, aryl), 7.38 (d, J = 8.9 Hz,1H, aryl), 7.22 (m, 5H, aryl), 7.12 (m, 2H, aryl), 6.87 (d, J = 7.5 Hz,1H, aryl), 6.71 (t, J = 7.6 Hz, 1H, aryl), 4.52 (br s, 1H, OH), 1.45 (s,9H, CH3). These spectroscopic data were in agreement with those reported in the literature [67].

With the complex challenges of chemical substances, we look forward to future research findings about 137848-28-3,belong chiral-catalyst compound

Reference£º
Article; Chen, Liang; Zhao, Ning; Wang, Qiuwen; Hou, Guohua; Song, Haibin; Zi, Guofu; Inorganica Chimica Acta; vol. 402; (2013); p. 140 – 155;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, [1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5 its synthesis route is as follows.,602-09-5

In a glass reactor equipped with a stirrer, a condenser, and a thermometer,180 g (0.629 mol) of (RS) -1,1′-bi-2-naphthol, 127 g (1.439 mol) of ethylene carbonate, 9.0 g of potassium carbonate and 180 g of toluene were charged and stirred at 110 C. for 10 hours. After 1300 g of toluene was added to the reaction product, the organic layer was washed with an aqueous solution of sodium hydroxide while maintaining the temperature at 80 C. Next, this organic layer was washed with water until the washing water became neutral. The obtained organic layer was dehydrated under reflux using a Dean Stark apparatus to obtain a toluene solution in which (RS) -2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene was dissolved. Thereafter, when the solution was cooled, crystals precipitated at 63 C. all at once, making it difficult to stir, 1200 g of toluene was added to make it into a slurry state containing crystals and allowed to stir, and then cooled further to 30 C. This was filtered and the crystals were further washed with 200 g of toluene, and the obtained crystals were dried to obtain 198 g of pale yellow crystals of (RS) -2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene The yield was 84.1%, the HPLC purity was 99.1%, the total content of organic substances having a boiling point of 250 C. or lower at 101.3 kPa: 0.1%). Differential scanning calorimetry and powder X-ray diffraction measurement were performed on the obtained crystals. The differential scanning calorimetry chart and the powder X-ray diffraction pattern of the obtained crystal are shown in FIGS. 1 and 2, respectively

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

Reference£º
Patent; TAOKA CHEMICAL COMPANY LIMITED; MATSUURA, TAKASHI; HIRABAYASHI, SHUNICHI; (8 pag.)JP2016/204293; (2016); A;,
Chiral Catalysts
Chiral catalysts – SlideShare