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Product Details of [ 313352-62-4 ]

CAS No. :313352-62-4 MDL No. :MFCD19701214
Formula : C10H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :TVESJBDGOZUZRH-SECBINFHSA-N
M.W : 161.20 Pubchem ID :12344035
Synonyms :

Safety of [ 313352-62-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 313352-62-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 313352-62-4 ]

[ 313352-62-4 ] Synthesis Path-Downstream   1~50

  • 1
  • ethyl 4-phenyl-4-aminobutanoate [ No CAS ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With porcine liver esterase In water at 30℃; various pH; Kcat/Km;
  • 2
  • [ 313352-62-4 ]
  • [ 23132-29-8 ]
YieldReaction ConditionsOperation in experiment
With α-D-glucose 6-phosphate; NADP; magnesium chloride In phosphate buffer at 37℃; Enzymatic reaction;
  • 3
  • [ 313352-62-4 ]
  • [ 74-88-4 ]
  • (R)-(+)-1-methyl-5-phenylpyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In tetrahydrofuran at 20℃; for 48h;
With sodium hydride In tetrahydrofuran at 20℃; for 48h;
  • 4
  • [ 948018-51-7 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With ammonium cerium(IV) nitrate In methanol; water at 25℃; for 12h;
  • 5
  • [ 948018-37-9 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen / (RFc)-1-Ph2P-2-((S)-MeO(2-Py)CH)ferrocene iridium complex / toluene; methanol / 6 h / 25 °C / 7500.75 Torr 2: Ce(NH4)2(NO3)6 / methanol; H2O / 12 h / 25 °C
  • 6
  • [ 313352-61-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
98% In methanol; dichloromethane Ethyl 4(R)-amino-4-phenylbutyrate (15). 5(R)-phenyl-2-pyrrolidinone (16). To a stirred solution of ethyl 4(R)-amino-4-phenylbutyrate (515 mg, 2.48 mmol) in 20 mL of anhydrous methanol was added sodium cyanide (25 mg, 0.5 mmol) at room temperature. The reaction mixture was stirred at 55° C. for 4 h, cooled to room temperature, concentrated under reduced pressure. The residue was taken up in methylene chloride, washed with water, brine, dried over anhydrous MgSO4, concentrated to afford 391 mg of product (98% yield) as a colorless crystal, mp 103-105° C. (lit.17 102-104° C.). 1 H NMR (CDCl3) δ 1.80-1.95 (m, 1H), 2.27-2.42 (m, 2H), 2.45-2.58 (m, 1H), 4.709 (t, 1H, J=7.2 Hz), 7.22-7.38 (m, 5H), 7.425 (br, 1H); 13 C NMR (CDCl3) δ 30.19, 30.93, 57.91, 125.34, 127.46, 128.56, 142.43, 178.85.
  • 7
  • [ 6270-17-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: titanium(IV) tetraethanolate / 72 °C / Inert atmosphere 2.1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-Amino-2-methyl-1-propanol; potassium <i>tert</i>-butylate / isopropyl alcohol / 50 °C / Molecular sieve 3.1: hydrogenchloride / methanol / 20 °C 3.2: 0.17 h / pH > 11
  • 8
  • ethyl 4-[(R)-tert-butylsulfinylimino]-4-phenylbutanoate [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-Amino-2-methyl-1-propanol; potassium <i>tert</i>-butylate / isopropyl alcohol / 50 °C / Molecular sieve 2.1: hydrogenchloride / methanol / 20 °C 2.2: 0.17 h / pH > 11
  • 9
  • C16H25NO3S [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C16H25NO3S With hydrogenchloride In methanol at 20℃; Stage #2: With ammonia; ammonium chloride; sodium hydroxide In water for 0.166667h;
  • 10
  • [ 1203050-38-7 ]
  • [ 76-05-1 ]
  • [ 313352-62-4 ]
  • C25H19N3O3*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57 mg Stage #1: 4-iodo-N-(quinolin-8-yl)benzamide; (R)-(+)-5-phenylpyrrolidin-2-one With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 140℃; for 2h; Inert atmosphere; Microwave irradiation; Stage #2: trifluoroacetic acid In 1,4-dioxane; water; acetonitrile
  • 11
  • [ 158800-60-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine hydrochloride; sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 3 h / 25 °C 3.1: water / tetrahydrofuran / 3 h / Reflux 4.1: water; potassium hydroxide / methanol / 22 h / 0 - 25 °C 4.2: 3 h / Reflux
  • 12
  • dimethyl (R)-2-(2-azido-2-phenylethyl)malonate [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloromethane / 3 h / 25 °C 2.1: water / tetrahydrofuran / 3 h / Reflux 3.1: water; potassium hydroxide / methanol / 22 h / 0 - 25 °C 3.2: 3 h / Reflux
  • 13
  • C31H30NO4P [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: water / tetrahydrofuran / 3 h / Reflux 2.1: water; potassium hydroxide / methanol / 22 h / 0 - 25 °C 2.2: 3 h / Reflux
  • 14
  • methyl 2-oxo-5-phenylpyrrolidine-3-carboxylate [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
51 mg Stage #1: methyl 2-oxo-5-phenylpyrrolidine-3-carboxylate With water; potassium hydroxide In methanol at 0 - 25℃; for 22h; Stage #2: In toluene for 3h; Reflux;
  • 15
  • 1-[(4-methoxyphenyl)methyl]-5-phenylpyrrolidin-2-one [ No CAS ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With Chiralpak IC In ethanol at 25℃; Resolution of racemate; 41; 42 Enantiomer 1 :(5R or S)-5-phenylpyrrolidin-2-one and enantiomer 2:(5S)-5-phenylpyrrolidin-2-one The title compounds were isolated by purification of Intermediate 20 under SFC conditions on Chiralpak IC (50*264 mm*mm, flow 360 mL/min, 25°C, CO2 + 20 % EtOH, injection of 7.6 mL, solution at a concentration of 100 gIL. The first eluting enantiomer (RT 6.2 mm) was collected and the fractions were evaporated to yieldenantiomer 1 (5R or S)-5-phenylpyrrolidin-2-one (arbitrarily attributed as the (5R) enantiomer, 5.34 g). The second eluting enantiomer (RT 9.0 mm) was collected and the fractions were evaporated to yield enantiomer 2 (5S or R)-5-phenylpyrrolidin-2-one (arbitrarily attributed as the (55) enantiomer, 5.58 g). 1H NMR (400 MHz, CDC13) ö 7.33 (m, 5H), 6.34 (m, 1 H), 4.75 (t, 1 H, J 7.0 Hz), 2.49 (m, 3 H), 1.97 (m, 1 H). LCMS (ESjRT 3.14 mm, 162.2 (M+H).
  • 16
  • (R)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-phenylethylcarbamic acid tert-butyl ester [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: (R)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-phenylethylcarbamic acid tert-butyl ester With hydrogenchloride In ethyl acetate at 10 - 20℃; Stage #2: With toluene-4-sulfonic acid In toluene for 4h; Reflux; 2.3 (3) (R)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-phenylethylcarbamic acid tert-butyl ester (150 g , 0.42 mol) was dissolved in ethyl acetate (0.7 L), the temperature was lowered to 10 ° C, and a saturated hydrogen chloride / ethyl acetate solution (0.7 L) was added dropwise thereto, keeping the internal temperature <10 deg. C. The reaction mixture was cooled to room temperature overnight and filtered to give 105 g of a white solid. The white solid was dissolved in toluene (0.7 L), p-toluenesulfonic acid (4.7 g, 0.025 mol) was added and the mixture was heated under reflux for 4 hours. The mixture was washed with saturated sodium bicarbonate (0.5 L * 3), brine (0.5 L * 1) and concentrated to give 49 g of a white solid in 73 % yield.
  • 17
  • [ 313352-62-4 ]
  • [ 56523-47-8 ]
YieldReaction ConditionsOperation in experiment
81% With lithium aluminium tetrahydride; In tetrahydrofuran; at -5 - 20℃; for 2h; (4) (R)-5-phenylpyrrolidin-2-one (40 g, 0.25 mol) was dissolved in tetrahydrofuran (800 mL), cooling to -5-5 deg. C, lithium aluminum hydride (23.6 g, 0.62 mol) was added in portions to keep the internal temperature below 10 C, and the mixture was stirred at room temperature for 2 h. Quenched with water (23.6 g), keeping the temperature within -5-5 deg. C, followed by stirring at room temperature for 1 h, filtered, and concentrated to give 30 g of a colorless oil, in 81% yield.
  • 18
  • [ 313352-62-4 ]
  • (R)-2-chloro-8-phenyl-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere
  • 19
  • [ 313352-62-4 ]
  • (R)-1-((4,4-difluorocyclohexyl)methyl)-4-(8-phenyl-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridin-2-yl)pyridin-2(1H)-one trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere 3.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 100 °C
  • 20
  • [ 313352-62-4 ]
  • (R)-8-phenyl-2-(2-((tetrahydro-2H-pyran-4-yl)methoxy)pyridin-4-yl)-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 95 °C 3.2: 18 h / 85 °C
  • 21
  • [ 313352-62-4 ]
  • C21H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere 3.1: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 18 h / 65 °C 3.2: 1 h / 20 °C
  • 22
  • [ 313352-62-4 ]
  • (R)-8-phenyl-2-(1-(pyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl)-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere 3.1: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 18 h / 65 °C / Inert atmosphere
  • 23
  • [ 313352-62-4 ]
  • C27H26F2N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / toluene / 1.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 110 °C 2.1: N,N`-dimethylethylenediamine; copper(l) iodide; potassium carbonate / acetonitrile / 14 h / 80 °C / Inert atmosphere 3.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 100 °C
  • 24
  • [ 62476-56-6 ]
  • [ 313352-62-4 ]
  • (R,Z)-2,6-dichloro-N-(5-phenylpyrrolidin-2-ylidene)pyridin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% (i?)-5-Phenylpyrrolidin-2-one (15.0 g, 93 mmol, Preparation 44) was suspended in toluene (460 mL) under nitrogen. The mixture was stirred at rt for about 30 min then cooled to about 0 °C. POCl3 (11.5 mL, 123 mmol) was added dropwise over about 2 min. After completion of addition the mixture was allowed to warm to rt. After about 90 min <strong>[62476-56-6]2,6-dichloropyridin-3-amine</strong> (15.5 g, 95 mmol) was added in one portion then the mixture was warmed to about 110 °C. After about 90 min, the reaction mixture was allowed to cool to rt and concentrated under reduced pressure to afford a brown solid. The residue was dissolved in DCM (600 mL) and washed successively with 2 N NaOH (300 mL), water (100 mL) and then sat. NaCl (300 mL). The aqueous layers were extracted with DCM (300 mL). The combined organic layers were dried over Na2SC>4, filtered and concentrated to give the title compound (27.2 g, 95percent); LC/MS (Table 1, Method z) Rt = 0.89 min; MS m/z: 306 (M+ H)+.
  • 25
  • [ 100-58-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; dichloromethane / -78 - 17 °C 1.2: 0.75 h / pH 3 - 4 2.1: Resolution of racemate
Multi-step reaction with 3 steps 1: tetrahydrofuran / 12 h / -40 °C / Autoclave; Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; iodine; hydrogen / 2,2,2-trifluoroethanol / 24 h / 20 °C / 37503.8 Torr / Autoclave; Inert atmosphere 3: ammonium cerium (IV) nitrate / acetonitrile; water / 12 h / 20 °C / Autoclave; Inert atmosphere
  • 26
  • [ 22050-10-8 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
1: 17% 2: 17% Resolution of racemate; 43; 44 Preparation 43 and 44: (1S)-5-phenylpyrrolidin-2-one and (i?)-5-phenylpyrrolidin-2-one The racemic mixture was separated via chiral SFC (Table 2, Method 11) to give (,S)-5-phenylpyrrolidin-2-one (14.03 g, 17%, OR = negative); LC/MS (Table 1, Method t) Rt = 2.81 min; MS m/z: 162 (M+H)+, lH NMR (400 MHz, CDC13) δ 7.39 - 7.25 (m, 5H), 6.07 (br. s., 1H), 4.74 (t, J=7.1 Hz, 1H), 2.63 - 2.33 (m, 3H), 2.03 - 1.89 (m, 1H) and (R)-5- phenylpyrrolidin-2-one (14.25 g, yield 17%, OR = positive); LC/MS (Table 1, Method t, OR = negative) Rt = 2.81 min; MS m/z: 162 (M+H)+, lH NMR (400MHz, CDC13) δ 7.39 - 7.25 (m, 5H), 6.01 (br. s., 1H), 4.74 (t, J=7.1 Hz, 1H), 2.64 - 2.32 (m, 3H), 2.04 - 1.89 (m, 1H).
  • 27
  • (R)-1-(4-methoxybenzyl)-5-phenylpyrrolidin-2-one [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
86% With ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 12h; Autoclave; Inert atmosphere;
  • 28
  • 5-hydroxy-1-(4-methoxybenzyl)-5-phenylpyrrolidin-2-one [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; iodine; hydrogen / 2,2,2-trifluoroethanol / 24 h / 20 °C / 37503.8 Torr / Autoclave; Inert atmosphere 2: ammonium cerium (IV) nitrate / acetonitrile; water / 12 h / 20 °C / Autoclave; Inert atmosphere
  • 29
  • [ 104-53-0 ]
  • [ 313352-62-4 ]
  • 5-phenyl-1-(3-phenylprop-1-en-1-yl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With acetic acid In toluene at 110℃; for 12h; Dean-Stark; Condensation Procedure B General procedure: From a modified procedure2, hydrocinnamaldehyde (2 equiv) and a cyclic lactam (1 equiv) were added to a solutionof 3:1 toluene:AcOH (0.25 M). A Dean-Stark trap was affixed to the flask and the reaction was stirred at 110 ° C toremove water via azeotropic distillation for 12 hours or until complete by TLC. After allowing the flask to cool toroom temperature, the reaction was quenched with a saturated solution of NaHCO3 and extracted twice with EtOAc.The organic layer was rinsed with a saturated NaCl solution and dried over MgSO4. The organic layer was thenconcentrated under vacuum and purified using flash chromatography on silica (EtOAc:Hexanes).
  • 30
  • [ 25333-24-8 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
88% With pyridoxal 5'-phosphate; transaminase ATA-303; isopropylamine In aq. phosphate buffer; acetonitrile at 45℃; for 24h; Enzymatic reaction; enantioselective reaction;
94 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; enantioselective reaction;
  • 31
  • [ 25333-24-8 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
48 % ee With pyridoxal 5'-phosphate; transaminase ATA-217; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 45℃; for 24h; Enzymatic reaction; enantioselective reaction;
77 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 95 percent; enantioselective reaction;
77 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 2-3 Comparative Example 2 General procedure: Using different ester substituents, such as Me, Et, iPr, tBu for the reaction, the reaction conditions are: when the aromatic ketone tert-butyl ester substrate is 0.2 mmol, 0.4 mmol ammonium acetate is used as the ammonia source, and 1 mol% Ru(3.3 e) (OAc) 2 is a catalyst, 0.4 mL of trifluoroethanol is added as a solvent, the pressure of hydrogen is 50 bar, and the reaction is carried out at 90° C. for 24 hours.
  • 32
  • 3-(3-phenylpropyl)-5H-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
92% With silver hexafluoroantimonate; C30H31ClN3O4RuS In 1,2-dichloro-ethane at 40℃; for 5h; Inert atmosphere; Glovebox; enantioselective reaction;
92% With silver hexafluoroantimonate; [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)] In 1,2-dichloro-ethane at 40℃; for 5h; Inert atmosphere; Glovebox; enantioselective reaction;
  • 33
  • 3-(3-phenylpropyl)-5H-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 68664-23-3 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
1: 83 % ee 2: 23 %Spectr. With silver hexafluoroantimonate; Noyori's catalyst In 1,2-dichloro-ethane at 40℃; for 5h; Inert atmosphere; Glovebox; enantioselective reaction;
1: 83 % ee 2: 23 %Spectr. With silver hexafluoroantimonate; Noyori's catalyst In 1,2-dichloro-ethane at 40℃; for 5h; Inert atmosphere; Glovebox; enantioselective reaction;
1: 84 % ee 2: 15 %Spectr. With C30H26N6Ru(2+)*2BF4(1-) In 1,2-dichloro-benzene at 20℃; for 8h; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 34
  • [ 1821-12-1 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: hydroxylamine hydrochloride; potassium carbonate / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 4: C30H31ClN3O4RuS; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: dichloromethane / 0.67 h / 20 °C 4: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: dichloromethane / 0.67 h / 20 °C 4: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
  • 35
  • [ 1821-12-1 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: hydroxylamine hydrochloride; potassium carbonate / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 4: Noyori's catalyst; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: dichloromethane / 0.67 h / 20 °C 4: silver hexafluoroantimonate; Noyori's catalyst / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 3: dichloromethane / 0.67 h / 20 °C 4: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methoxybenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 20 °C 3.1: C33H35ClIrN3O3 / water / 12 h / 20 °C
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique 2.1: hydroxylamine hydrochloride / water; ethyl acetate / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2.2: 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 3.1: C30H26N6Ru(2+)*2BF4(1-) / 1,2-dichloro-benzene / 8 h / 20 °C / Inert atmosphere; Schlenk technique

  • 36
  • [ 18496-54-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; potassium carbonate / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 3: C30H31ClN3O4RuS; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 3 steps 1: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 0.67 h / 20 °C 3: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 3 steps 1: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 0.67 h / 20 °C 3: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
  • 37
  • [ 18496-54-3 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; potassium carbonate / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 3: Noyori's catalyst; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 3 steps 1: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 0.67 h / 20 °C 3: silver hexafluoroantimonate; Noyori's catalyst / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 3 steps 1: potassium carbonate; hydroxylamine hydrochloride / ethyl acetate; water / 12 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 0.67 h / 20 °C 3: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methoxybenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / water; ethyl acetate / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 1.2: 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: C30H26N6Ru(2+)*2BF4(1-) / 1,2-dichloro-benzene / 8 h / 20 °C / Inert atmosphere; Schlenk technique

  • 38
  • [ 32153-46-1 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 2: C30H31ClN3O4RuS; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: dichloromethane / 0.67 h / 20 °C 2: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: dichloromethane / 0.67 h / 20 °C 2: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
  • 39
  • [ 32153-46-1 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.67 h / 20 °C 2: Noyori's catalyst; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: dichloromethane / 0.67 h / 20 °C 2: silver hexafluoroantimonate; Noyori's catalyst / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: dichloromethane / 0.67 h / 20 °C 2: [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methoxybenzenesulfonamide)]; silver hexafluoroantimonate / 1,2-dichloro-ethane / 5 h / 40 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: C33H35ClIrN3O3 / water / 12 h / 20 °C

  • 40
  • [ 313352-62-4 ]
  • (4R)-4-(methylamino)-4-(phenyl)butyric acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: (R)-(+)-5-phenylpyrrolidin-2-one With potassium hydroxide In methanol for 5h; Reflux; Stage #2: With hydrogenchloride In methanol; water at 20℃;
83% Stage #1: (R)-(+)-5-phenylpyrrolidin-2-one With potassium hydroxide In methanol Reflux; Stage #2: With hydrogenchloride In methanol; water
  • 41
  • 3-(3-phenylpropyl)-5H-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 68664-23-3 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
1: 14 %Spectr. 2: 62 %Spectr. With silver hexafluoroantimonate; [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-nitrobenzenesulfonamide)] In 1,2-dichloro-ethane at 40℃; for 12h; Inert atmosphere; Glovebox; enantioselective reaction;
  • 42
  • 3-(3-phenylpropyl)-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
75 % ee With silver hexafluoroantimonate; [RuCl(p-cymene)(N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methoxybenzenesulfonamide)] In 1,2-dichloro-ethane at 40℃; for 5h; Inert atmosphere; Glovebox; Overall yield = 76 %Spectr.; enantioselective reaction;
96 %Spectr. With C33H35ClIrN3O3 In water monomer at 20℃; for 12h; enantioselective reaction;
82 % ee With C50H54ClIrN4O5 In water monomer at 20℃; Overall yield = 98 percent; General procedure: Specifically, the following steps are included: The compound of formula IV: the compound of formula V is added to the solvent F at a molar ratio of 1:50 to 100, and the reaction is carried out at 10 to 40 degrees with stirring for 1 to 24 hours to obtain a compound of formula VI The solvent F is a mixed solvent of one of hexafluoroisopropanol, trifluoroethanol, hexafluoroisopropanol or trifluoroethanol with water, and the molar ratio of the hexafluoroisopropanol or trifluoroethanol with water The ratio is 1: 0 to 10; the concentration of the compound of formula IV in the solvent F is 0.1 to 1 mol / L.
84 % ee With C30H26N6Ru(2+)*2F6P(1-) In 1,2-dichloro-ethane at 20℃; for 24h; Overall yield = 82 percent;

  • 43
  • [ 2051-95-8 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
  • 44
  • [ 2051-95-8 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 91 percent; Optical yield = 38 percent ee; enantioselective reaction;
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: hydrogen; ammonium acetate; ruthenium bis(acetate) / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave
38 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 2 General procedure: Using different ester substituents, such as Me, Et, iPr, tBu for the reaction, the reaction conditions are: when the aromatic ketone tert-butyl ester substrate is 0.2 mmol, 0.4 mmol ammonium acetate is used as the ammonia source, and 1 mol% Ru(3.3 e) (OAc) 2 is a catalyst, 0.4 mL of trifluoroethanol is added as a solvent, the pressure of hydrogen is 50 bar, and the reaction is carried out at 90° C. for 24 hours.

  • 45
  • [ 6270-17-3 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 95 percent; Optical yield = 83 percent ee; enantioselective reaction;
83 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 2 General procedure: Using different ester substituents, such as Me, Et, iPr, tBu for the reaction, the reaction conditions are: when the aromatic ketone tert-butyl ester substrate is 0.2 mmol, 0.4 mmol ammonium acetate is used as the ammonia source, and 1 mol% Ru(3.3 e) (OAc) 2 is a catalyst, 0.4 mL of trifluoroethanol is added as a solvent, the pressure of hydrogen is 50 bar, and the reaction is carried out at 90° C. for 24 hours.
  • 46
  • [ 104750-69-8 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 96 percent; Optical yield = 88 percent ee; enantioselective reaction;
88 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 2 General procedure: Using different ester substituents, such as Me, Et, iPr, tBu for the reaction, the reaction conditions are: when the aromatic ketone tert-butyl ester substrate is 0.2 mmol, 0.4 mmol ammonium acetate is used as the ammonia source, and 1 mol% Ru(3.3 e) (OAc) 2 is a catalyst, 0.4 mL of trifluoroethanol is added as a solvent, the pressure of hydrogen is 50 bar, and the reaction is carried out at 90° C. for 24 hours.
  • 47
  • [ 55666-45-0 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
99% With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 1 Example 1 General procedure: The reaction conditions are: when the aromatic ketone tert-butyl ester substrate is 0.2 mmol, 0.4 mmol ammonium acetate is used as the ammonia source, 1 mol% Ru(3.3e)(OAc)2 is used as the catalyst, and 0.4 mL of trifluoroethanol and hydrogen are added. The pressure was 50 bar, and the reaction was carried out at 90°C for 24 hours. 99% yield, 94% ee.
96% With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; enantioselective reaction;
  • 48
  • [ 55666-45-0 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With ruthenium bis(acetate); ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 93 percent; Optical yield = 89 percent ee; enantioselective reaction;
71 % ee With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; 3 General procedure: a When the aromatic ketone tert-butyl vinegar substrate is 0.2mmol, use 0.4mmol acetic acid as the ammonia source, and 1mol% metal complex The compound is a catalyst, 0.4mL of trifluoroethanol is added as a solvent, the pressure of hydrogen is 50bar, and the reaction is at 90°C for 24h.
  • 49
  • [ 23132-29-8 ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; ammonium acetate; hydrogen In 2,2,2-trifluoroethanol at 90℃; for 24h; Autoclave; Overall yield = 95 percent; Optical yield = 16 percent ee; enantioselective reaction;
  • 50
  • C18H16F3NO3 [ No CAS ]
  • [ 56553-09-4 ]
  • [ 313352-62-4 ]
YieldReaction ConditionsOperation in experiment
89.6 % ee With 2,2-bis[2-[4(S)-p-tolyl-1,3-oxazolinyl]]propane; 3-amino-7-dimethylamino-2-methylphenazine hydrochloride; N-ethyl-N,N-diisopropylamine In Hexafluorobenzene at 60℃; for 12h; Inert atmosphere; Irradiation; Overall yield = 25 percent; 1 General procedure: At room temperature, a chiral bidentate oxazoline Box (0.02 mmol) was added to a dry nitrogen-protected reaction tube, and the substrate (0.2 mmol, the default was p-trifluoromethylbenzoyl-protected substrate if not labeled). ), organic photocatalyst neutral red (0.004mmol), solvent perfluorobenzene (8mL), then diisopropylethylamine (0.2mmol) was added, and then reacted at 60°C under the irradiation of 5w blue LED for 12 The product was isolated by column chromatography after 1 hour.
89.6 % ee With 2,2-bis[2-[4(S)-p-tolyl-1,3-oxazolinyl]]propane; 3-amino-7-dimethylamino-2-methylphenazine hydrochloride; N-ethyl-N,N-diisopropylamine In Hexafluorobenzene at 60℃; for 12h; Inert atmosphere; Irradiation; Overall yield = 25 percent; 1 General procedure: At room temperature, a chiral bidentate oxazoline Box (0.02 mmol) was added to a dry nitrogen-protected reaction tube, and the substrate (0.2 mmol, the default was p-trifluoromethylbenzoyl-protected substrate if not labeled). ), organic photocatalyst neutral red (0.004mmol), solvent perfluorobenzene (8mL), then diisopropylethylamine (0.2mmol) was added, and then reacted at 60°C under the irradiation of 5w blue LED for 12 The product was isolated by column chromatography after 1 hour.
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