Category: chiral-catalyst

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 17-iodo-5alpha-androsta-16-ene 1 (0.5 mmol), 2,2′-diamino-1,1′-binaphthalene 2 (varied from 1.0 mmol to 0.125 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (3 20 mL), 5% hydrochloric acid (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to give a solid material. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200 mm), EtOAc/CHCl3 or hexane/CHCl3 (the exact ratios are specified in Section 4.4 for each compound). 4.3. Characterisation of the products (Fig. 3) (Sax)-3: Yield: 410 mg (72%). Off-white yellow solid, mp 137-142 C; [Found: C, 84.55; H, 7.65; N, 4.70; C40H44N2O requires C,84.46; H, 7.80; N, 4.93]; Rf (5% EtOAc/CHCl3) 0.68. 1H NMR (CDCl3) delta: 8.94 (1H, d, 9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.94 (1H, d,8.2 Hz, H-50), 7.87 (1H, d, 8.5 Hz, H-300), 7.82 (1H, d, 7.5 Hz, H-400), 7.43 (1H, dt, 6.3 Hz, 1.6 Hz, H-60), 7.35 (1H, s, NH), 7.31 (1H, dt,8.5 Hz, 0.8 Hz, H-70), 7.29-7.26 (2H, m, H-600 , H-600), 7.23 (1H, dt,6.8 Hz, 1.1 Hz, H-700), 7.16 (1H, d, 8.7 Hz, H-80), 6.96 (1H, d, 8.2 Hz,H-800), 6.21 (1H, dd, 2.9 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.7 Hz, 6.5 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd,16.7 Hz, 11.9 Hz, 1.4 Hz, 15-CHaHb), 1.07-0.54 (23H, m, skeleton protons), 0.78 (3H, s, 19-CH3), 0.62 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.6, 150.4, 143.0, 140.0, 135.7, 133.8, 132.5. 131.1, 130.3, 129.3, 128.3, 128.2, 128.1, 127.5, 126.8, 125.3, 124.9, 123.6, 122.8, 120.4, 119.7, 118.1, 110.5, 56.8, 54.7, 47.2, 45.3, 38.4, 36.3, 34.2, 33.7, 31.8, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 16.0, 12.1. IR (KBr, m(cm1)): 3440 (amide-NH), 3398 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (relint.): 551.4 (29), 285.2 (100). [alpha]D20 = 37.1 (c 1.34, CHCl3). (Rax)-3: Yield: 114 mg (20%). Off-white solid substance; [Found:C, 84.30; H, 7.66; N, 4.77; C40H44N2O requires C, 84.46; H, 7.80; N,4.93]; Rf (5% EtOAc/CHCl3) 0.72. 1H NMR (CDCl3) delta: 8.95 (1H, d,9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.93 (1H, d, 7.9 Hz, H-50), 7.87 (1H, d, 8.9 Hz, H-300), 7.82 (1H, d, 7.8 Hz, H-400), 7.43 (1H, dt,6.4 Hz, 1.2 Hz, H-60), 7.36 (1H, s, NH), 7.31 (1H, dt, 8.6 Hz, 0.8 Hz,H-70), 7.29-7.26 (2H, m, H-6”, H”), 7.23 (1H, dt, 6.9 Hz, 1.5 Hz,H-7”), 7.16 (1H, d, 8.5 Hz, H-8′), 6.96 (1H, d, 8.4 Hz, H-8”), 6.21 (1H, dd, 3.1 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.3 Hz, 6.4 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd, 16.6 Hz,11.7 Hz, 2.0 Hz, 15-CHaHb), 1.07-0.53 (23H, m, skeleton protons), 0.77 (3H, s, 19-CH3), 0.31 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.5, 150.4, 143.1, 140.2, 135.7, 133.8, 132.4, 131.1, 130.3, 129.3, 128.4, 128.3, 128.2, 127.5, 126.8, 125.3, 124.9, 123.6,122.8, 120.4, 119.7, 118.0, 110.6, 56.8, 54.8, 47.2, 45.2, 38.4, 36.3, 34.2, 33.7, 31.7, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 15.5, 12.1. IR(KBr, m (cm1)): 3441 (amide-NH), 3396 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (rel int.): 551.4 (29), 285.2 (100). [alpha]D20 = +191.5 (c 0.914, CHCl3). (Sax)-4: Yield: 102 mg (12%). Beige solid substance; [Found: C,84.31; H, 8.35; N, 3.12; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.69. 1H NMR (CDCl3) alpha: 8.94 (2H, d,9.2 Hz, H-3′), 8.08 (2H, d, 9.2 Hz, H-4′), 7.95 (2H, d, 8.2 Hz, H-5′),7.46 (2H, dt, 7.2 Hz, 0.9 Hz, H-6′), 7.35 (2H, dt, 7.2 Hz, 0.9 Hz, H-7′), 7.1 (2H, d, 9.3 Hz, H-8′), 7.13 (2H, s, NH), 6.05 (2H, dd, 3.1 Hz, 1.5 Hz, H-16), 2.02 (2H, ddd, 16.8 Hz, 6.4 Hz, 3.1 Hz, 15-CHaHb), 1.88 (2H, dd, 9.9 Hz, 3.1 Hz, 14-CH), 1.75 (2H, ddd, 16.8 Hz,11.7 Hz, 1.5 Hz, 15-CHaHb), 1.69-0.54 (44H, m, skeleton protons), 0.77 (6H, s, 19-CH3), 0.57 (6H, s, 18-CH3). 13C NMR (CDCl3) alpha: 163.6, 150.2, 140.0, 136.0, 135.2, 132.4, 131.3, 130.0, 128.2,127.5, 125.3, 124.9, 120.5, 118.1, 56.6, 54.8, 47.2, 45.4, 38.4, 36.3, 34.2, 33.6, 31.7, 31.4, 29.0, 28.8, 26.8, 22.1, 20.5, 16.1, 12.1. IR (KBr, m (cm1)): 3408 (amide-NH), 1677 (CON), 1621 (CC). MS m/z (rel int.): 853.6 ((M+H)+); 875.6 ((M+Na)+), 891.5 ((M+K)+). [alpha]D20 = +12.0 (c 0.418, CHCl3). (Rax)-4: Yield: 85 mg (10%). Beige solid substance; [Found: C,84.28; H, 8.30; N, 3.06; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.74. 1H NMR (CDCl3) alpha: 8.95 (2H, d,9.0 Hz, H-3′), 8.08 (2H, d, 9.0 Hz, H-4′), 7.96 (2H, d, 7.8 Hz, H-5′), 7.46 (2H, dt, 7.8 Hz, 0.9 Hz, H-6’…

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

Reference£º
Article; Mikle, Gbor; Boros, Borbla; Kollr, Lszl; Tetrahedron Asymmetry; vol. 25; 23; (2014); p. 1527 – 1531;,
Chiral Catalysts
Chiral catalysts – SlideShare

173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Pd(OAc)2 (0.110 g, 0.50 mmol) and SIMes.HCl (0.170 g, 0.50 mmol) were dissolved in THF (15 mL). The resulting mixture was heated to 55 C along with magnetic stirring for 2 h. After cooling down the mixture to RT, it was purified on silica-gel column. The resulting orange solution was transferred to the Schlenk tube and the solvent was removed under vacuum. The oily residue was dissolved in CH2Cl2 (5 mL) and water (3-10 mL) was added to remove unreacted SIMes.HCl. Organic phase was separated and hexane (5 mL) was slowly added. After 24 h the product was filtered off and dried in vacuum. Yield: 50%. Crystals suitable for X-ray analysis were obtained by slow evaporation of the CH2Cl2/hexane solution. 1H NMR (500 MHz; CDCl3;TMS): delta=6.92 (s, 8H, ArH), 6.77 (s, 8H, NCH2-NCH2), 2.47 (s, 12H, p-ArCH3), 1.94 (s, 24H, oArCH3) 13C NMR (125 MHz; CDCl3; TMS): delta=170.9 (s, N2C), 137.5 (s, NC), 136.1 (s, o-CCH3), 135.7 (s, p-CCH3), 128.8 (s, CH), 122.4 (s, CH2), 21.25 (s, o-CH3), 18.9 (s, p-CH3) elemental analysis calcd (%) C42H52Cl4N4Pd2: C 52.14, H 5.42, N 5.79; found: C 51.15, H 5.09, N 5.30., 173035-10-4

The synthetic route of 173035-10-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gorna, Marta; Szulmanowicz, Micha? S.; Gniewek, Andrzej; Tylus, W?odzimierz; Trzeciak, Anna M.; Journal of Organometallic Chemistry; vol. 785; (2015); p. 92 – 99;,
Chiral Catalysts
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It is a common heterocyclic compound, the chiral-catalyst compound, trans-Cyclohexane-1,2-diamine, cas is 1121-22-8 its synthesis route is as follows.,1121-22-8

General procedure: Aryl halide (1.0 equiv) and aliphatic diamines/amino alcohol (2.0 equiv) were taken in a 100 ml round bottom flask along with 100-150 mg of the chitosan copper catalyst in CH3CN (15 ml) solvent. The resultant mixture was heated at reflux for 3-6 h. After completion of the reaction (the complete consumption of starting materials was confirmed by TLC) the reaction mixture was extracted with ethylacetate. The separated organic phase was concentrated to get the gummy liquid product 3. The chitosan copper catalyst was collected by simple decanting off the reaction mixture. The recovered catalyst was then washed thoroughly with ethyl acetate 2-3 times,dried under vacuum at 50C and used for another run.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Article; Bodhak, Chandan; Kundu, Ashis; Pramanik, Animesh; Tetrahedron Letters; vol. 56; 2; (2015); p. 419 – 424;,
Chiral Catalysts
Chiral catalysts – SlideShare

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

IPr-HCI (82.04 mg, 0.193 mmol), [Pd(cin)(M-CI)]2 (50.0 mg, 0.096 mmol), a magnetic stir bar and acetone (0.8 mL) were charged into a vial . The mixture was stirred at 60 C for 1 h . The solvent was removed and the product was dried under vacuum . The product was obtained as a dark orange powder in a 99% ( 132 mg) yield . Single crystals were grown by vapour diffusion of hex- ane into a solution of the complex in DCM . XH IMMR (400 MHz, CDCh) : delta (ppm) = 9.19 (s, 1 H), 8.32 (d, J = 1.60 Hz, 2H), 7.56-7.52 (m, 2H), 7.46 (d, J = 7.44 Hz, 2H), 7.33 (d, J = 7.75 Hz, 4H), 7.21 (m, 3H), 5.66 (s, 1 H), 4.46 (s, 1 H), 3.83 (s, 1 H), 2.90 (s, 1 H), 2.48- 2.41 (m, 4H), 1.27 (d, J = 6.81 Hz, 12H), 1.19 (d, J = 6.76 Hz, 12H) . 13C {XH } NMR (100 MHz, CDCh): delta (ppm) = delta 144.9 (C), 136.7 (CH), 131.8 (C), 129.7 (C), 128.4 (CH), 127.7 (CH), 127.5 (CH), 124.5 (CH), 105.0 (C), 28.8 (CHs), 24.4 (CHs), 23.7 (CHs) . Elemental analysis: Expected : C 63.02, H 7.05 N 4.08 Found : C 62.92 H 7.14 N 4.15

250285-32-6 is used more and more widely, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Patent; UMICORE AG & CO. KG; NOLAN, Steven P.; (47 pag.)WO2018/115029; (2018); A1;,
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: C8H14ClNO264,mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added N-phenyl glycinonitrile (0.264 g, 2 mmol) in CH3CN followed by the addition of 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, cycloheptylamine (0.25 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 pressure. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield 143, (0.300 g, 33percent) mp 53-55¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 6.9 min, 94.1percent purity; MS (ESI): m/z 449 (M+H, 100), 381 (1.2), 353 (16.2), 226 (19.9), 225 (54.3), 212 (20.5), 177 (18.3), 164 (9.6).

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; 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
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO41,mainly used in chemical industry, its synthesis route is as follows.,602-09-5

7H-Dibenzo[c,g]carbazole (12c): 30 g (0.105 mol) of 1,1′-binaphthalene-2,2′-diol (BINOL), 30 g (0.224 mol) of (NH4)2SO3¡¤H2O and 90 ml of 26 % NH4OH was heated at 200C in a 160 ml autoclave (Parr Instrument) for 5 days (after 48 h the pressure dropped from 45 to 18 bar). Upon cooling down, the crude matter was washed with boiling water, dissolved in a 1:1 mixture of EtOH:HCl (conc.), extracted with hot toluene (3×200 ml) and concentrated under vacuum. Residual starting material was removed by extraction with 2M NaOH solution (3×200 ml). Organic layers were combined, dried over Na2SO4, filtered, concentrated and chromatographed on a SiO2 column (50 % DCM in hexanes). Yield: 7.7 g (27 %) of dark-yellow crystalline solid. M.p. 154-156C. 1H NMR (CDCl3, 300 MHz): delta 9.22 (d, J=8.5, 2H), 8.79 (br, s, 1H), 8.05 (dd, J=8.1, 1.3, 2H), 7.89 (d, J=8.7, 2H), 7.74-7.65 (m, 4H), 7.53 (ddd, J=8.0, 6.9, 1.0, 2H).

With the synthetic route has been constantly updated, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol,belong chiral-catalyst compound

Reference£º
Article; Kerner, Luka?; Gmucova, Katarina; Ko?i?ek, Jozef; Pet?i?ek, Vaclav; Putala, Martin; Tetrahedron; vol. 72; 44; (2016); p. 7081 – 7092;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.

To a mixture of BINAM (852 mg, 3.0 mmol) and HOAc (1.8 Ml, 30mmol) was added acetic anhydride (312 muL, 3.3 mmol), and the solution was stirred at room temperature overnight. NaOH was added until pH > 7 to quench the reaction, and the solution was extracted with DCM (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-1; yield: 880 mg (89%).

4488-22-6, The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
Chiral catalysts – SlideShare

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

To anhydrous1,4-dioxane (20 mL), [Pd(acac)2] 1 g (3.3 mmol,1 equiv) and IPrHCl 1.56 g (3.7 mmol, 1.1 equiv) were added. The mixture was refluxed for 24 h. After reaction,solvent was evaporated under vacuum. Then, dichloromethane was added and stirred until no more soliddissolved. The solution was filtered and dichloromethane was removed under vacuum. Yellow powder obtained was washed with diethyl ether and dried under vacuum. Yellow solids, yield: 85%, 1H NMR (399.78 MHz, CDCl3 delta 7.49(t, 2H), 7.32 (m, 4H), 7.10 (s, 2H), 5.10 (s, 1H), 2.94 (td,4H), 1.81 (d, 6H), 132 (d, 12H), 1.08 (12H), 13C NMR(100.53 MHz, CDCl3) delta 186.70, 183.61, 155.98, 146.61,135.05, 130.42, 125.30, 124.20, 99.46, 28.54, 27.13,26.36, 23.07.

250285-32-6 is used more and more widely, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Article; Lee, Dong Jin; Kim, Myungwoong; Kim, Chan Kyung; Lee, Ik Mo; Bulletin of the Korean Chemical Society; vol. 40; 7; (2019); p. 710 – 718;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.602-09-5,[1,1′-Binaphthalene]-2,2′-diol,as a common compound, the synthetic route is as follows.

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)., 602-09-5

602-09-5 [1,1′-Binaphthalene]-2,2′-diol 762831, achiral-catalyst compound, is more and more widely used in various fields.

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 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: The silver(I) N-heterocyclic carbene complexes Ag(I)-NHCs were synthesized according to the Lin?s Ag2O method. To a solution of 1 mmol of NHC precursors (1,3-disubstituted imidazolinium chloride salts) in 5 mL of DCM, 0.5 mmol of Ag2O was added and the mixture was stirred at room temperature for 18 h. Later the reaction mixture was filtered through a celite and concentrated under vacuo to obtain the desired Ag(I)-NHC catalysts as a white crystalline solids.

With the complex challenges of chemical substances, we look forward to future research findings about 141556-45-8,belong chiral-catalyst compound

Reference£º
Article; Thirukovela, Narasimha Swamy; Balaboina, Ramesh; Kankala, Shravankumar; Vadde, Ravindhar; Vasam, Chandra Sekhar; Tetrahedron; vol. 75; 18; (2019); p. 2637 – 2641;,
Chiral Catalysts
Chiral catalysts – SlideShare