Category: chiral-catalyst

14098-24-9, Benzo-18-crown 6-Ether is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A modification of the previously reported procedure23 was used. Commercially available Eaton’s reagent (ca. 8 ml that corresponds to 6.28 mmol of phosphorus(V) oxide) and acetic acid (0.20 ml, 3.45 mmol) were mixed at room temperature. Then naphtho-15-crown-5 ether (1 g, 3.14 mmol) was added. The reaction mixture was stirred at room temperature for ca. 6 h and then poured into water. The suspension was extracted with dichloromethane and the combined organic phases were washed with water. Removal of the dried (MgSO4) solvent gave a dark brown oil, which upon repeated extractions with hot heptane, afforded the product as an off-white solid (1.02 g, 90%), mp 126-129 C., 14098-24-9

The synthetic route of 14098-24-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Paramonov, Sergey V.; Lokshin, Vladimir; Smolentsev, Artem B.; Glebov, Evgeni M.; Korolev, Valeri V.; Basok, Stepan S.; Lysenko, Konstantin A.; Delbaere, Stephanie; Fedorova, Olga A.; Tetrahedron; vol. 68; 38; (2012); p. 7873 – 7883;,
Chiral Catalysts
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A common heterocyclic compound, the chiral-catalyst compound, name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine,cas is 22795-99-9, mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

(S)-(-)-4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide 95 g of 2-methoxy-4-amino-5-ethylsulphonylbenzoic acid dissolved in 370 ml of acetone, in the presence of 37 g of trielthylamine, is treated with 40 g of ethyl chloroformate with 57 g of (S)-(-)-1-ethyl-2-aminomethylpyrrolidine. 115 g of (S)-(-)-N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-ethylsulphonylbenzamide is obtained (yield=84%).

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Reference£º
Patent; Sanofi-Synthelabo; US6169094; (2001); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

A common heterocyclic compound, the chiral-catalyst compound, name is 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide,cas is 7181-87-5, mainly used in chemical industry, its synthesis route is as follows.,7181-87-5

The reagent and solvent shown below were placed in a 50 mL flask under nitrogen flow. F13: 274 mg (1.00 mmol) (purchased from Sigma-Aldrich) Dehydrated DMF: 10 ml.After the solution was degassed with nitrogen, 192 mg (4.00 mmol) of sodium hydride (60% oil dispersion) was added and stirred for 2 minutes. Thereafter, 112 mg (1.00 mmol) of potassium tert-butoxide was added, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, 30 ml of water degassed with nitrogen while stirring was gradually added to precipitate the desired product, and then the solvent was removed with a silane. After the addition of 20 ml of de-gassed water with nitrogen, the solvent was removed twice with distilled water, and 10 ml of hexane degassed with nitrogen was added, followed by dispersion washing using an ultrasonic washing machine , And was filtered through a membrane filter. It was confirmed that the filtrate partially deliquesced. Thereafter, drying was carried out at 50 C. under reduced pressure to obtain 116 mg (yield 40%) of Comparative Compound 3 as a black brown solid.

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Reference£º
Patent; CANON INCORPORATED; MIYASHITA, HIROKAZU; NISHIDE, YOSUKE; KAMATANI, JUN; (41 pag.)JP2017/8011; (2017); A;,
Chiral Catalysts
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A common heterocyclic compound, the chiral-catalyst compound, name is 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,cas is 250285-32-6, mainly used in chemical industry, its synthesis route is as follows.,250285-32-6

In a glove box, a Schlenk flask equipped with a magnetic bar is loaded with the imidazolium salt IPr EtaC1 (2.96 g, 7 mmol), Pd(acac), (1.53 g, 5 mmol) and dry dioxane (100 mL). The flask was taken outside the glove box and placed in an oil bath at 100 C over a magnetic stirrer for 6 hours. After that time, the solution looked clear with no solid remaining. The solvent was evaporated in vacuo and diethyl ether was added until no more solid was dissolved. The solution is filtered and the solid washed with diethyl ether (2 x 10 mL). The solvent was evaporated in vacuo to yield 2.99 g (95 %) of the desired compound as a yellow powder.1H NMR (delta, 400 MHz, CDCl3): 7.51 (t, / = 7.8 Hz, 2H), 7.35 (d, / = 7.8 Hz, 4H), 7.12 (s, 2H), 5.12 (s, IH), 2.95 (q, / = 6.4 Hz, 4H), 1.84 (s, 3H), 1.82 (s, 3H), 1.34 (d, / = 6.4 Hz, 12H), 1.10 (d, / = 6.4 Hz, 12H). EPO 13C NMR (delta, 100 MHz, CDCl3): 187.1, 184.1, 156.4, 147.0, 135.5, 134.8, 130.9, 125.7, 124.7, 124.6, 99.9, 29.1, 30.0, 27.6, 26.8, 23.7, 23.5.Anal. Calcd. for C32H43ClN2O2Pd (MW 629.57): C, 61.05; H, 6.88; N, 4.45. Found: C, 60.78; H, 7.15; N: 4.29.

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Reference£º
Patent; PROMERUS LLC; WO2006/128097; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

A common heterocyclic compound, the chiral-catalyst compound, name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine,cas is 22795-99-9, mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

General procedure: 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 1.2 equivalents) was added to a solution of the corresponding alpha-methyl carboxylic acid (2) (1 equiv), the appropriate amine (1.5 equiv) and DIEA (2 equiv) in dry acetonitrile (10 mL) at room temperature under argon atmosphere. The reaction mixture was stirred at room temperature overnight. Solvent was evaporated under reduced pressure, and the crude product was purified using a Teledyne Isco Combiflash? Rf purification machine using 0-10percent CHCl3/methanol as eluent to provide the desired amides 3-59 in 68-95percent yields.

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Article; Mathew, Bini; Snowden, Timothy S.; Connelly, Michele C.; Guy, R. Kiplin; Reynolds, Robert C.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2136 – 2142;,
Chiral Catalysts
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A common heterocyclic compound, the chiral-catalyst compound, name is 1,3-Dimesityl-1H-imidazol-3-ium chloride,cas is 141556-45-8, mainly used in chemical industry, its synthesis route is as follows.,141556-45-8

Prepared according a procedure of Mohr et al.21 To a soln of1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (175 mg,0.513 mmol) in CH2Cl2 (10 mL) was added HgO (108 mg,0.514 mmol) and Me4NCl (56.4 mg, 0.51 mmol). After stirring at r.t. for 15 h, the soln was passed through Celite, the solvent was removed in vacuo, and the residue was washed with H2O (2 ¡Á 10 mL) and Et2O (2 ¡Á 10 mL) to give 14 as a colorless solid; yield: 240 mg (82%); mp 270 C (dec); Rf = 0.09 (CH2Cl2-MeOH, 10:1).

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Article; Emsermann, Jens; Arduengo, Anthonyj.; Opatz, Till; Synthesis; vol. 45; 16; (2013); p. 2251 – 2264;,
Chiral Catalysts
Chiral catalysts – SlideShare

A common heterocyclic compound, the chiral-catalyst compound, name is 1,4,7,10,13-Pentaoxacyclopentadecane,cas is 33100-27-5, mainly used in chemical industry, its synthesis route is as follows.,33100-27-5

To the sodium salt of 2-nitroimidazole prepared above was added acetonitrile (50 ml), 15-crown-5-ether (3.5 ml, 14.3 mmol) and 4-bromo-2-methyl-2-butene (2 ml; 17.4 mmol). The mixture was stirred at RT for ca 16 h. and then the solvent was removed to leave a crude semi-solid which was purified by column chromatography on silica. The intermediate product, 1-(3-methyl-2-butenyl)-2-nitroimidazole (80percent yield) was eluted using a mixture of petroleum ether (40-60)/ethyl acetate (ratio 4:1 respectively).

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Reference£º
Patent; Amersham International plc; US5993774; (1999); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

The chiral-catalyst compound, cas is 22795-99-9 name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

Example 24 (S)-(-)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-3,6-dibenzyloxy-2-methoxybenzamide (Method A) A solution of 3,6-dibenzyloxy-2-methoxybenzamide acid (120 mg, 0.33 mmol), thionyl chloride (120 mg, 1 mmol) and two drops of dimethylformamide as catalyst in 5 ml toluene was stirred at 60¡ã C. for 1.5 h. The solvent was evaporated and the residue dissolved in CH2 Cl2 and evaporated again. This residue was dissolved in 8 ml CH2 Cl2 and a solution of (S)-(-)-1-ethyl-2-aminomethylpyrrolidine (65 mg, 0.5 mmol) in 2 ml CH2 Cl2 was added. After stirring overnight at room temperature the solvent was evaporated and the residue partitioned between 2M HCl and ether. The aqueous phase was made alkaline, extracted with CH2 Cl2, dried (Na2 SO4) and evaporated to give a crude product. Purification by chromatography on SiO2 with iPr2 O/hexane/MeOH/NH3 69:20:10:1 as eluent gave 145 mg (93percent) pure title compound. M.p. 121¡ã-123¡ã C. [alpha ]D22 =-42¡ã (c=2.8, acetone). 1 H NMR (CDCl3)delta7.39 and 7.38)two s, CH2 Ph), 6.89 and 6.59 (AB, 4-H and 5-H), 5.06 and 5.03 (two s, CH2 Ph), 3.95 (s, OMe) ppm. Mass spectrum (EI, 70 eV): m/z 474 (M, 0.13percent), 347 (ArCO, 0.33percent), 98 (100percent), 91 (12percent)

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Reference£º
Patent; Astra Lakemedel Akteibolag; US5240957; (1993); A;,
Chiral Catalysts
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The chiral-catalyst compound, name is 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, mainly used in chemical industry, its synthesis route is as follows.,351498-10-7

Compound Int-1a (733 mg, 1.33 mmol) was suspended in ethanol (10 mL) and the resulting suspension was heated to 80 C. and allowed to stir for 5 minutes. Compound Int-1b (236 mg, 1.33 mmol) was then added and the resulting reaction was allowed to stir at 80 C. for an additional 2 hours. The reaction was then cooled to room temperature using in an ice bath and the reaction mixture was filtered. The collected red solid was dried under vacuum to provide compound Int-1c (579 mg, 72%).

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Patent; MERCK SHARP & DOHME CORP.; Girijavallabhan, Vinay; Njoroge, F. George; Bogen, Stephane; Kerekes, Angela; Bennett, Frank; Huang, Ying; Nair, Latha; Pissarnitski, Dmitri; Verma, Vishal; Dang, Qun; Davies, Ian; Olsen, David B.; Stamford, Andrew; Vacca, Joseph P.; US2014/161770; (2014); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33100-27-5,1,4,7,10,13-Pentaoxacyclopentadecane,as a common compound, the synthetic route is as follows.

General procedure: A solution of (2 mmol, 0.4 ml) of 15-crown-5 in (10 ml) of absolute ethanol was added to a solution of (1 mmol, 0.933 gm Pr-picrate), (0.936 gm Nd-picrate) and (0.900 gm Dy-picrate) in (10 ml) of absolute ethanol and refluxed at (50 ? 60 oC) for (1 hr.). The solution was concentrated at (40 ? 50 oC) to a very small volume (till the formation of a precipitate), usually a gummy precipitate forms which was treated with (40 ? 60 oC) petroleum ether until all the gummy precipitate was converted to a fine yellow ? orange powder. The precipitate was collected and stored in a desicator for complete dryness. These complexes were also prepared by another method, by stirring a solution of 15-crown-5 with a solution of lanthanide picrate for (24 ? 48 hrs.). The gummy precipitates were treated with petroleum ether. The yields were (92 ? 96percent)24., 33100-27-5

As the paragraph descriping shows that 33100-27-5 is playing an increasingly important role.

Reference£º
Article; Al-Amery, Mohammed H. A.; Al-Abdaly, B. Ibrahim; Albayaty, M. Kahtan; Oriental Journal of Chemistry; vol. 32; 2; (2016); p. 1025 – 1048;,
Chiral Catalysts
Chiral catalysts – SlideShare