Tag: M.W:200-300

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

General procedure: To a two-neckedround-bottomed flask (50 mL) equipped with a three-way stopcock and a magnetic stir bar, was added diamine 1a (56.8 mg, 0.2 mmol) under the air. The vessel was capped with a rubber septum, evacuated,and refilled with N2 gas for three times, and MeCN (20 mL) was added through the septum. The resulting solution was cooled to -40 C. To the solution, was added DIH (151.9 mg, 0.4 mmol) under a stream of N2 gas at -40 C. The resulting solution was stirred for 7 h before quenched with aqueous Na2S2O3 solution (1.0 M, 20 mL), and the resulting mixture was extracted with CH2Cl2 (20 mL ¡Á 3). The combined organic extracts were dried over Na2SO4 and concentrated under vacuum to give the crude product, which was purified by flash column chromatography (eluent: hexane/EtOAc 5:5) on NH silica gel to give product 2a (38.9 mg, 69%). Further purification was carried out by recrystallization from acetone.

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Reference£º
Article; Okazaki, Masato; Takahashi, Kosuke; Takeda, Youhei; Minakata, Satoshi; Heterocycles; vol. 93; 2; (2016); p. 770 – 782;,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5

To 18.3 g of sodium hydride was added 50 g (0.175 mol) of 2,2′-dihydroxy-1,1′-dinaphthyl and stirred under nitrogen in 1.0 L of dry tetrahydrofuran (THF). After 1 hour, 116 g of chloromethyl methyl ether was added to the heavy precipitate and the resulting mixture was stirred for about 12 hours and then filtered through a pad of celite. The filtrate was shaken with 500 ml of water and 1 L of methylene chloride. An aqueous layer formed and was extracted two times more with methylene chloride. The combined organic layers were washed with water saturated with potassium bicarbonate. The organic layer was dried and filtered through a squat column of alumina and the column filtrate was evaporated until crystals appeared. The crude product was purified on a silica gel column by elution with a methylene chloride/hexane solution. About 53.5 g (63%) of 2,2′-bis(methoxymethoxy)-1,1′-dinaphthyl, m.p 93-94 C., 0.11 mol was collected. [00053] Next, 171 ml of 1.6 N butyllithium in hexane was added to a mixture of 41 g of the above bisacetal in 1 L of tetrahydrofuran and stirred under nitrogen at 0 C. for 45 minutes. The reaction mixture was then allowed to warm to 25 C. and 25.8 ml of dimethyl sulfate was added to the suspension and the mixture was stirred for 12 hours. About 30 ml of water saturated with sodium carbonate was added and the solvent was evaporated under reduced pressure at 50 C. [00054] The residue, in 300 ml of methylene chloride, was washed twice with water. An additional 300 ml of methylene chloride, 300 ml of methanol, and 25 ml of concentrated hydrochloric acid was added to the organic solution. The solution was stirred for 3 hours, and the solvent was evaporated. The yellow product was recrystallized from methylene chloride-hexane and was purified on a silica gel column (methylene chloride, hexane 1:1) to give 29.5 g (86%) of (R)-3-3′-dimethyl-2,2′-dihydroxy-1,1′-dinaphthyl, m.p. 204-206 C.; 1HNMR:2.2(s.6H), 7.1(d.2H), 7.3(m.2H), 7.4(m.2H), 7.8(m.4H).

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Patent; IBC Advanced Technologies, Inc.; US6686479; (2004); B2;,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,4488-22-6

General procedure: To an oven-dried Schlenk flask were added diamine 3 (1.0 equiv),Pd2(dba)3 (5 mol%), rac-BINAP (10 mol%), NaOtBu (3.0 equiv), and toluene under Ar atmosphere.Then 8-haloqunoline 4 (2.2 equiv) was added directly. The flask was sealed, and the reaction wasstirred at 85 C until the complete consumption of the starting material 3. The mixture was cooled toroom temperature, filtered through a silica plug, and the plug was washed with EA. The combinedfiltrates were concentrated under reduced pressure, and the residue was purified by silica gelchromatography to give the desired product Ln.

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Article; Liu, Wen-Bo; Usman, Muhammad; Wu, Lin-Yang; Molecules; vol. 25; 4; (2020);,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,4488-22-6

General procedure: In a typical experiment, Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), 2-iodobornene 3 (0.5 or 1mmol), 2,2?-diamino-1,1?-binaphthalene (0.25 or 0.5mmol) and triethylamine (0.5ml) were dissolved in DMF (10mL) under argon in a 100mL 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 carried out for the given reaction time with stirring at 50C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20ml) and washed with water (3x20mL), 5% hydrochloric acid (20mL), saturated NaHCO3 (20mL) and brine (20mL). The organic phase was dried over Na2SO4, filtered and evaporated to a solid material. After doing an NMR analysis, all compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm), EtOAc/CHCl3 or EtOAc/hexane/CHCl3 eluent (the exact ratios are specified in Characterisation (Section 4.4) for each compound).

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

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Article; Mikle, Gabor; Boros, Borbala; Kollar, Laszlo; Tetrahedron Asymmetry; vol. 27; 9-10; (2016); p. 377 – 383;,
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.23190-16-1,(1R,2S)-2-Amino-1,2-diphenylethanol,as a common compound, the synthetic route is as follows.

To a 5 L round bottom flask equipped with an overhead stirrer, thermocouple and distillation head, was charged 550 g (2.579 mol) of (1 R,2S)- diphenyl-2-aminoethanol, 457 g (3.868 mol, 1.5eq) of diethylcarbonate, 18 g (0.258 mol, 0.1 eq) of NaOEt in 100 mL of EtOH and 3.5 L of toluene. The reaction was heated until an internal temperature of 90C was reached and EtOH distillation began. The reaction was refluxed until an internal temperature of 110C was reached (7 hours). For every 500 mL of solvent that was removed via the distillation head, 500 mL of toluene was added back to the reaction. A total of about 1.6 L of solvent was removed. The reaction was allowed to cool to room temperature and then filtered on a 3 L coarse fritted funnel with 2 psig N2. Nitrogen was blown over the cake overnight (at)o give 580 g (94% yield) of the titled nom””””” ””d” 9,-..C.U.(at), l:(at)VQ”; ‘I <"Q'.(at)(at) Up(at),.,; ',r1" (at)'(at) (at) (at).(at).(at) (at)-77 1'Cf'; 41i), ..(at)(at) ^(at)''1 I or(at)r(at)1 (at),f3rr:.(at)i ....u..(at) " ' (at).V.(at)_7(at)dli (at) ",-JVV Jc;;;J7Jv (at)L.-, U- -(at)t 'H'o(at)(at)-:J """.v (at)' "(at)(at) fUSD5 -/: q,78V;",j (at)(at)-j -(at), t(at).3J(at):, (at):_/(at).:::: , OJ (at), :=: ?Q(at)':::'::' 23190-16-1, As the paragraph descriping shows that 23190-16-1 is playing an increasingly important role.

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Patent; PFIZER PRODUCTS INC.; WO2005/102389; (2005); A2;,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5

General procedure: Separately, each of the dihydroxy-substituents, catechol (a), 2,3-dihyroxynaphthalene (b), 2,2′-dihydroxy-1,1′-bisnaphthalene (c) (50 mmol), and NaOH (0.12 mol) were dissolved in 20-25 ml ethanol and 2-chloroethanol (0.12 mol) was added to this solution dropwise over 15 min. After refluxing the reaction mixture for 20 h, the resulting solid was separated by filtration. Ethanol was evaporated in vacuo and the resulting oily product was dissolved in 200 ml chloroform. The chloroform solution was washed with 3% NaOH and then with distilled water until the pH reached neutrality.

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Article; Kertmen, Ahmet; Szczygelska-Tao, Jolanta; Chojnacki, Jaros?aw; Tetrahedron; vol. 69; 49; (2013); p. 10662 – 10668;,
Chiral Catalysts
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(1R,2S)-2-Amino-1,2-diphenylethanol, cas is 23190-16-1, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,23190-16-1

5.0 mL of water and 0.21 mL of 1 N hydrochloric acid was added to 90 mg (0.21 mmol) of a mixture of a sodium salt of (3S)-3-benzyloxycarbonylamino-(R)-1-amino(sulfoamino)phosphinyl-2-piperidone and a sodium salt of (3R)-3-benzyloxycarbonylamino-(S)-1-amino(sulfoamino)phosphinyl-2-piperidone at about 1:1, and 42.6 mg (0.20 mmol) of (1R, 2S)-(-)-2-amino-1,2-diphenylethanol; and the reaction liquid was stirred while being heated. Both compounds were completely dissolved at an inner temperature of about 50C, heating was stopped, and the reaction liquid was left till the inner temperature becomes room temperature. The precipitated crystal was taken through a filter, and 25 mg of a salt of (3R)-3-benzyloxycarbonylamino-(R)-1-amino(sulfoamino) phosphinyl-2-piperidone with (1R,2S)-(-)-2-amino-1,2-diphenylethanol (0.040 mmol, an optical purity (d.e.) of 95%, and a yield of 19%) was obtained. salt of (3R)-3-benzyloxycarbonylamino-(R)-1-amino(sulfoamino)phosphinyl-2-piperidone with (1R,2S)-(-)-2-amino-1,2-diphenylethanol1H-NMR (200MHzFT, TMS, CD3OD) 1.63-2.02 (3H, m), 2.12-2.30 (1H, m), 3.50-3.88 (2H, m), 4.17-4.30 (1H, m), 4.46 (1H, d, J=4.0 Hz), 5.08 (2H, s), 5.22 (1H, d, J=4.0 Hz), 7.04-7.41 (15H, m)

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Patent; Nippon Kayaku Kabushiki Kaisha; ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI; EP1457494; (2004); A1;,
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.602-09-5,[1,1′-Binaphthalene]-2,2′-diol,as a common compound, the synthetic route is as follows.

602-09-5, [ 1 , 1 ,-Binaphthalene]-2,2′-diol (30.0 g, 0. 1 05 mo I, 1 .0 eq. ) was placed in a flask and flushed with argon. Anhydrous toluene (300 m L ) was added, followed by trifluoromethanesulfonic acid (1 1.7 ml., 0.2 1 0 mo I, 2.0 eq. ). After further degassing, the mixture was re fluxed for 48 hours. After cool ing, the organic layer was extracted with water (500 m l. ), dried over gSO i, and reduced under vacuum until precipitation. Hexane (300 ml.) was then added, and the resulting suspension was stirred for 2h before being filtered off. This solid was dissolved in DC I, and filtered over silica (elution with hexane / DCM 2 : 1 ). The volume of the fraction obtained was reduced to ca. 50 m l., and the resulting crystals were filtered off, yielding the title compound.

The synthetic route of 602-09-5 has been constantly updated, and we look forward to future research findings.

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Patent; NOVALED GMBH; DENKER, Urlich; ZOeLLNER, Mike; GRAeF, Katja; SENKOVSKYY, Volodymyr; WALLIKEWITZ, Bodo; SCHOLZ, Johannes; FREY, Julien; (143 pag.)WO2016/180891; (2016); A1;,
Chiral Catalysts
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A common heterocyclic compound, the chiral-catalyst compound, name is (1R,2S)-2-Amino-1,2-diphenylethanol,cas is 23190-16-1, mainly used in chemical industry, its synthesis route is as follows.,23190-16-1

A solution of (Boc)2O (44 mmol) in THF (50ml) was added to the mixture of the amino alcohol (40 mmol) and sodium carbonate (80 mmol) in THF/H2O (1/1, 300 ml) at O0C. The mixture was stirred at O0C for Ih and then at room temperature for another two 2h (TLC was used to monitor the reactions). Water (200 ml) was added to the mixture upon completion. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers was washed with brine (300 ml) and dried with anhydrous MgSO4 for Ih. It was then filtered and the solvent was removed under vacuum to give the product (yield = 90 – 99 %). It was sufficiently pure for the next step. The pure product was obtained by recrystallization from the THF and hexane, or by purification with silica gel chromatography.Example 2.1: Tert-butyl (lS,2R)-2-hydroxy-l,2-diphenylethylcarbamatePh PhBocHN OHYield: 90 %. 1H NMR (CD2Cl2): delta 7.25-7.27 (m, 6H), 7.08-7.1 1 (m, 4H), 5.33 (m, IH), 5.04 (m, IH), 4.92 (b, IH), 2.60 (b, IH), 1.38 (s, 9H).

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Patent; KANATA CHEMICAL TECHNOLOGIES INC.; WO2008/148202; (2008); A1;,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5

In a glass reactor equipped with a stirrer, cooler and thermometer,286 g (1 mol) of (RS) -1,1′-bi-2-naphthol;194 g (2.2 mol) of ethylene carbonate,Charge 15 g of potassium carbonate and 450 g of toluene,The reaction was performed at 110 C. for 10 hours. After diluting the reaction solution by adding 540 g of toluene,The organic solvent layer was washed by adding 290 g of a 10% by mass aqueous sodium hydroxide solution.Subsequently, the washing with water was repeated using 500 g of water until the washed water became neutral. After washing with water, trisodium phosphate dodecahydrate 1. 6 g was added and the mixture was stirred for 30 minutes. Thereafter, the mixture was cooled from 80 C. to 30 C. at a rate of 0.5 C./min, filtered under reduced pressure (50 kPa) and dried,(RS) -2,2′-bis (2-hydroxyethoxy)-1,1′-binaphthalene317 g (yield: 84.5% by mass, purity: 99.6%, D50: 58 mum) of white crystals of the compound were obtained. The phosphorus content in the obtained crystals was 47 mass ppm.

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Patent; DKS Co Ltd; Saito, Daisuke; Umeda, Kazutoshi; (9 pag.)JP6615397; (2019); B1;,
Chiral Catalysts
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