Category: chiral-catalyst

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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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

Preparation of Cobalt(II) ComplexA 50 mL flask was charged with N,N’-bis(3,5-di-tert-butylsalicylidene)-l, 1,2,2- tetramethylethenediamine (0.4302 g, 0.78 mmol, 1.0 equiv), EtOH (17 mL), and Co(OAc)2 (0.1385 g, 0.78 mmol, 1.0 equiv). The mixture was degassed and then heated to reflux under nitrogen for 3 h, cooled to room temperature. The precipitate was filtered and the purple solid was washed with EtOH (10 mL) and dried under high vacuum to give 0.3533 g (75%) of the cobalt(II) complex.

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Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; WO2010/91067; (2010); A2;,
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(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

(S)-ethyl 2-(2,6-(UfIuOrO-S-JOdOnJCOtJnOyI)-S-(Tl -ethylpyrrolidin-2-yl)methylamino)acrylateEthyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 37, 0.500 g, 1.10 mmol) was taken up THF (40 mL) and cooled to 0 0C for 10 min and then (S)-(I- ethylpyrrolidin-2-yl)methanamine (0.153 mL, 1.10 mmol) was added and stirred at room temperature for 2 min. The reaction mixture was quenched with sat NH4Cl diluted with EtOAc and separated, dried, and solvent removed. The residue was purified by a 0-5percent gradient on the ISCO of DCM/Methanol to give (S)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3- ((l-ethylpyrrolidin-2-yl)methylamino)acrylate (0.36Og, 67percent) as a red oil. MS (ES) (M+H)+: 494 for Ci8H22F2IN3O3

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Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIFULCO, Neil; CHOY, Allison, Laura; QUIROGA, Olga; SHERER, Brian; WO2010/136817; (2010); A1;,
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1,3-Dimesityl-1H-imidazol-3-ium chloride, cas is 141556-45-8, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,141556-45-8

V-heterocyclic carbenes were synthesized from their corresponding imidazolium or imidazolinium salts (see Table 1 ). About 0.8 eq. of potassium tert- butoxide (8.9 mg) and 1 eq. of a 1 , 3-disubstituted imidazolium salt (Table 1 , entries 1 – 5) or 1 , 3-disubstituted imidazolinium salt (Table 1 , entry 7) was dissolved in 2 ml_ of tetrahydrofuran (THF). The reaction was stirred for 1 h under argon protection at ambient temperature. The solvent was then removed in vacuo. The resulting carbene was used without further purification and was characterized by 1H NMR and mass spectrometry.

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Patent; SOUTHERN ILLINOIS UNIVERSITY CARBONDALE; WO2008/70756; (2008); A2;,
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7181-87-5,7181-87-5, 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A reaction vessel was charged with 1,3 dimethyl benzimidazole iodide (0.28 g, 1.0 mmol), silver(I) oxide (0.23 g,1.0 mmol), and 30 mL of dichloromethane. The reaction was heated at reflux in the absence of light for 20 h. The reaction solution was filtered through Celite to remove the formed solids, and the solvent was removed under reduced pressure. Yield: 0.16 g.

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Article; Miecznikowski, John R.; Bernier, Nicholas A.; Van Akin, Christopher A.; Bonitatibus, Sheila C.; Morgan, Maura E.; Kharbouch, Rami M.; Mercado, Brandon Q.; Lynn, Matthew A.; Transition Metal Chemistry; vol. 43; 1; (2018); p. 21 – 29;,
Chiral Catalysts
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7181-87-5,7181-87-5, 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: General Method: To a 20 mL solution of 1.1 equivalents of nickelocene (41 mg, 0.22 mmol) in anhydrous THF, the respective imidazolium NHC precursor (0.2 mmol) was added as a solid. The resulting suspension was then refluxed for 4 h. The general method was modified for 4, 5 and 6. The reactions involving the formation of more electron-deficient 4 and 5 required 10 h at reflux with 2 equivalents of nickelocene (75 mg, 0.4 mmol). Synthesis of 6 was achieved after 16 h of reflux in the presence of 2.6 equivalents of nickelocene (98 mg, 0.52 mmol). The compounds were then purified by column chromatography. Details available in the Supporting information.

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Reference£º
Conference Paper; Luca, Oana R.; Thompson, Bennett A.; Takase, Michael K.; Crabtree, Robert H.; Journal of Organometallic Chemistry; vol. 730; (2013); p. 79 – 83;,
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1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, cas is 173035-10-4, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,173035-10-4

General procedure: An oven-dried Schlenk flask was charged with NHC salt 1 (2.49mmol) and evacuated for 30 min. The flask was then transferredinto a nitrogen-filled glove box and isolated KH (2.49 mmol)was added. The flask was then attached to a Schlenk line(argon/vacuum), evacuated once, and filled with argon. AnhydrousTHF (30 mL) was added, and the slow evolution of hydrogenwas observed. The resulting solution was then allowed tostir for 20 h at r.t. after which time the reaction mixture was filteredthrough a dry filter stick into an oven-dried Schlenk flask.The THF was evaporated, and the resulting free carbene wasextracted into anhydrous toluene (30 mL). The resulting toluenesolution was filtered through another dry filter stick into a previouslyevacuated and oven-dried Schlenk flask containing[(cod)Ir(py)2]PF6 (2, 1.66 mmol). The reaction was allowed tostir for 2 d at r.t. under an argon atmosphere. After this time, themixture was filtered to yield the desired iridium complex 3.

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Article; Cross, Paul W. C.; Herbert, John M.; Kerr, William J.; McNeill, Alan H.; Paterson, Laura C.; Synlett; vol. 27; 1; (2016); p. 111 – 115;,
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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 mixture of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride(0.425 g, 1.0 mmol), [Cp*IrCl2]2 (0.398 g, 0.5 mmol), and K2CO3(0.484 g, 3.5 mmol) in anhyd THF (8 mL)-CH2Cl2 (2 mL) wasstirred at 24 C for 10 h under N2. The resulting suspension wasstirred at 60 C for 24 h under N2, then concentrated to dryness. Afterthe addition of CH2Cl2 (10 mL) to the residue, the resulting suspensionwas filtered through Celite. The filtrate was concentrated todryness to give the iridium complex 2 as a brownish orange solid(0.748 g, 0.963 mmol, 96%).IR (ATR, ZnSe): 1659 cm-1 (CO2).1H NMR (500 MHz, CD2Cl2): delta = 7.43 (t, J = 8.0 Hz, 2 H), 7.33 (d,J = 8.0 Hz, 4 H), 7.09 (s, 2 H), 2.99-2.94 (m, 4 H), 1.45 (d, J = 7.0Hz, 12 H), 1.21 (s, 15 H), 1.06 (d, J = 6.0 Hz, 12 H).13C{1H} NMR (126 MHz, CD2Cl2): delta = 168.1, 165.9, 138.1, 130.1,126.4, 124.2, 87.2, 29.0, 27.2, 23.5, 9.4.Anal. Calcd for C38H51IrN2O3¡¤H2O: C, 57.48; H, 6.73; N, 3.53.Found: C, 57.40; H, 6.54; N, 3.57.

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Article; Yamada, Yoichim. A.; Ohta, Hidetoshi; Yuyama, Yoshinari; Uozumi, Yasuhiro; Synthesis; vol. 45; 15; (2013); p. 2093 – 2100;,
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N,N’-Bis(salicylidene)-1,2-propanediamine, cas is 94-91-7, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,94-91-7

A mixture of H2salipn (28.2mg, 0.100mmol) and [Ru(PPh3)3Cl2] (95.8mg, 0.100mmol) inTHF (30mL) was refluxed with stirring for 6 h, during which there was a color changefrom brown to dark green. The solvent was evaporated in vacuo, and the residue waswashed with diethyl ether (5mL 2) and hexane (5mL 2). Recrystallization fromCH2Cl2/hexane afforded black block crystals of 11.5CH2Cl2 in 7 days. Yield: 33.4mg,55.6% (based on Ru). IR (KBr disc, cm-1): 1594 (C=N), 1314 (Ar-O); MS (FAB): m/z 679[M], 644 [M – Cl], 417 [M – PPh3]. Anal. Calcd. for C35H31N2O2PClRu1.5(CH2Cl2) (%): C,54.41; H, 4.26; N, 3.48. Found: C, 54.47; H, 4.23; N, 3.50.

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Article; Ji, Jiao; Chen, Xin; Wang, Chang-Jiu; Jia, Ai-Quan; Zhang, Qian-Feng; Journal of Coordination Chemistry; vol. 72; 3; (2019); p. 480 – 490;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2133-34-8,(S)-Azetidine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Step A. N-(2-Thiophene-sulfonyl)-azetidine-2(S)-carboxylic Acid To a magnetically stirred mixture of azetidine-2(S)-carboxylic acid (1.0 g, 10 mmol) and Na2CO3 (2.1 g, 20 mmol) in 30 mL of water at 0 C. was added thiophene-2-sulfonyl chloride (1.8 g, 10 mmol), and the reaction was allowed to slowly warm up to room temperature overnight. The reaction was quenched by careful addition of concentrated HCl at 0 C. to pH above 2, and the product was extracted with EtOAc (3*15 mL). The extracts were dried over Na2SO4, and concentrated to dryness to provide the title compound as a white solid, which is >90% pure by 1H-NMR and used without further purification. 400 MHz 1H NMR (CD3OD): delta 2.2-2.4 (m, 2H), 3.7-3.9 (m, 2H), 4.42 (dd, 1H), 7.30 (dd, 1H), 7.75 (dd, 1H), 7.95 (dd, 1H)., 2133-34-8

As the paragraph descriping shows that 2133-34-8 is playing an increasingly important role.

Reference£º
Patent; Merck & Co., Inc.; US6645939; (2003); B1;,
Chiral Catalysts
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