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Product Details of [ 52780-14-0 ]

CAS No. :52780-14-0 MDL No. :MFCD00021863
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 201.06 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 52780-14-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.08
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 2.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.08
Solubility : 0.168 mg/ml ; 0.000837 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.469 mg/ml ; 0.00233 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.12
Solubility : 0.154 mg/ml ; 0.000767 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 52780-14-0 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:1987
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 52780-14-0 ]

* 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.

  • Upstream synthesis route of [ 52780-14-0 ]
  • Downstream synthetic route of [ 52780-14-0 ]

[ 52780-14-0 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 52780-14-0 ]
  • [ 65130-46-3 ]
YieldReaction ConditionsOperation in experiment
80% With phosphorus tribromide In dichloromethane at 20℃; for 16 h; Example 168; 4-[4-[l-(3-Bromo-phenyl)-eihoxy]-2-(^yrido[23-d]pyrimidin-4-ylarnino)-phenylsulfanyl]-phenol; Example 168a; 1 -( 1 -Bromo-ethyl)-4-fluoro-benzene; [0612] To a solution of l-(3-Bromo-phenyl)-ethanol (7.0 g, 34.0 mmol) in dichloromethane (40 mL) was added drop wise phosphorus tribromide (77 g, 34.0 mmol) .The mixture was stirred at room temperature for 16 h. The reaction was poured onto ice/water. The aqueous phase was made basic with sodium bicarbonate. The aqueous phase was extracted with dichloromethane. The organic phase was washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (7.8 g, 80 percent).
Reference: [1] Patent: WO2007/76034, 2007, A2, . Location in patent: Page/Page column 168
  • 2
  • [ 52780-14-0 ]
  • [ 2725-82-8 ]
Reference: [1] Chemische Berichte, 1982, vol. 115, # 2, p. 540 - 577
  • 3
  • [ 52780-14-0 ]
  • [ 1798-85-2 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1966, p. 218 - 222[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1966, # 2, p. 240 - 245
  • 4
  • [ 2142-63-4 ]
  • [ 52780-14-0 ]
  • [ 134615-22-8 ]
YieldReaction ConditionsOperation in experiment
97% With trans-[OsCl2(py){2,6-bis[4’-(S)-isopropyloxazolin-2-yl]pyridine}]; caesium carbonate In isopropyl alcohol at 82℃; for 4 h; Inert atmosphere; Schlenk technique General procedure: The catalyst [0.4 mol percent (complexes 12-22) or 0.2 mol percent (dinuclearcomplex 24)] and the ketone (2.5 mmol) were placed in a three-bottomSchlenk flask under dry argon atmosphere and 2-propanol (45 mL) wasadded. After stirring the mixture for 15 min at 82 °C, 5 ml of a 0.06Msolution of base (Cs2CO3) in 2-propanol (0.3 mmol) were added. Thereaction was monitored by gas chromatography using an HP-6890equipment. The corresponding alcohol and ketone were the only productsdetected in all cases. The conversion and e.e.values were determinedby GC with a Supelco β-DEX 120 chiral capillary column.
95% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H35FeN2P; hydrogen; potassium carbonate In methanol at 20℃; for 12 h; Glovebox; Autoclave General procedure: In a nitrogen-filled glovebox, a stainless steel autoclave was charged with [Ir(COD)Cl]2(3.4 mg, 0.005 mmol) andL2(6.6 mg, 0.11 mmol) in 1.0 mL of dry MeOH. After stirring for 1h at room temperature, a solution of the substrates1(1.0 mmol) andK2CO3(6.9 mg, 0.05 mmol) in 2.0 mL of MeOH was added to the reaction mixture, and then the hydrogenation was performed at room temperature under an H2pressure of 20 bar for 12 h. The solvent was then evaporated and the residue was purified by flash column chromatography to give the corresponding hydrogenation product which was analyzed by chiral HPLC to determine the enantiomeric excesses.
4% ee With formic acid; C23H32ClN2O2RuS; triethylamine In acetonitrile at 20℃; for 480 h; General procedure: To a ketone (2.4 mmol) placed in a vial 1 mL of CH3CN solution of the preformed ruthenium catalyst (24 μmol) and formic acid/triethylamine azeotropic mixture (1 mL) were added. The mixture was then stirred at room temperature and the progress of the reaction was monitored by TLC until the specified conversion was achieved. After evaporation of the solvents, 4 mL of CH2Cl2 and 1.5 mL of 10percent aqueous HCl solution were added to the residue. The layers were separated and the water layer was extracted twice with 2 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent was evaporated in vacuo. The residual oil was purified by column chromatography on silica gel using chloroform (dried over CaCl2) as eluent to afford the appropriate alcohol. The enantiomeric excess was determined by GC analysis using a Supelco cyclodextrin β-DEX 120 capillary column (20 m × 0.25 mm ID and 0.25 μm film thickness). The results of the reduction are summarized in Table 1.
80% ee With formic acid; C23H32ClN2O2RuS; triethylamine In acetonitrile at 20℃; for 24 h; General procedure: To a ketone (2.4 mmol) placed in a vial 1 mL of CH3CN solution of the preformed ruthenium catalyst (24 μmol) and formic acid/triethylamine azeotropic mixture (1 mL) were added. The mixture was then stirred at room temperature and the progress of the reaction was monitored by TLC until the specified conversion was achieved. After evaporation of the solvents, 4 mL of CH2Cl2 and 1.5 mL of 10percent aqueous HCl solution were added to the residue. The layers were separated and the water layer was extracted twice with 2 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent was evaporated in vacuo. The residual oil was purified by column chromatography on silica gel using chloroform (dried over CaCl2) as eluent to afford the appropriate alcohol. The enantiomeric excess was determined by GC analysis using a Supelco cyclodextrin β-DEX 120 capillary column (20 m × 0.25 mm ID and 0.25 μm film thickness). The results of the reduction are summarized in Table 1.
82 % ee With formic acid; C23H30ClN2O2RuS; triethylamine In acetonitrile at 20℃; for 18 h; General procedure: To a ketone (2.4 mmol) placed in a vial, 1 mL of CH3CN solution of preformed ruthenium catalyst (24 lmol) and formic acid/triethylamine azeotropic mixture (1 mL) were added. The mixture was then stirred at room temperature and the progress of the reaction was monitored by TLC until the specified conversion was achieved. After evaporation of the solvents, 4 mL of CH2Cl2 and 1.5 mL of 10percent aqueous HCl solution were added to the residue. The layers were separated and the water layer was extracted twice with 2 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent was evaporated in vacuo. The oily residue was purified by column chromatography on silica gel using chloroform (dried over CaCl2) as eluent to afford the appropriate ketone. The enantiomeric excess was determined by GC analysis using a Supelco cyclodextrinb-DEX 120 capillary column (20 m 0.25 mm I.D. and 0.25 lm film thickness).
56 % ee With formic acid; C23H32ClN2O2RuS; triethylamine In acetonitrile at 20℃; for 96 h; General procedure: To a ketone (2.4 mmol) placed in a vial, 1 mL of CH3CN solution of preformed ruthenium catalyst (24 lmol) and formic acid/triethylamine azeotropic mixture (1 mL) were added. The mixture was then stirred at room temperature and the progress of the reaction was monitored by TLC until the specified conversion was achieved. After evaporation of the solvents, 4 mL of CH2Cl2 and 1.5 mL of 10percent aqueous HCl solution were added to the residue. The layers were separated and the water layer was extracted twice with 2 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent was evaporated in vacuo. The oily residue was purified by column chromatography on silica gel using chloroform (dried over CaCl2) as eluent to afford the appropriate ketone. The enantiomeric excess was determined by GC analysis using a Supelco cyclodextrinb-DEX 120 capillary column (20 m 0.25 mm I.D. and 0.25 lm film thickness).
86.6 % ee With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (RC,SFc)-1-[bis(3,5-di-tert-butylphenyl)phosphino]-2-[1-N-(6-methylpyridin-2-ylmethyl)aminoethyl] ferrocene; potassium <i>tert</i>-butylate; hydrogen In ethanol at 25 - 30℃; for 18 h; Autoclave General procedure: To a 20 mL hydrogenation vessel were added the catalyst precursor [{Ir(cod)Cl}2] (1.7 mg, 2.53 μmol), ligand 2f (4.5 mg, 6.06 μmol), and anhydrous EtOH (3 mL) under a nitrogen atmosphere. The mixture was stirred for 1.0 h at 25–30 °C to give a clear yellow solution. After placing the vessel in an autoclave, the ketone (10 mmol) and t-BuOK (28 mg, 0.253 mmol) were added. The autoclave was replaced with H2 three times, and the reaction mixture was stirred at room temperature until no obvious hydrogen pressure drop was observed. After releasing the hydrogen pressure, the reaction mixture was filtered through a short silica gel column. The solvent in the filtrate was removed to determine the yield and the product obtained was analyzed by HPLC to determine the enantiomeric excess.
85 % ee With dichloro(mesitylene)ruthenium(II) dimer; (1S,2R)-1-((E)-(3-(dimethyl(phenyl)silyl)-2-hydroxy-5-methoxybenzylidene)amino)-2,3-dihydro-1H-inden-2-ol; sodium formate In water at 30℃; for 48 h; Schlenk technique General procedure: In a Schlenk tube, the chiral ligand (0.05mmol) and the metallic precursor (0.025mmol) were dissolved in water (4mL). After one hour of stirring at 30°C, sodium formate (10mmol) and the ketone (1mmol) were added to the aqueous solution. The solution was maintained at 30°C until total reduction of the ketone. The formed alcohol was separated from the catalyst by simple extraction with pentane (2×8mL), and the organic layer was dried over MgSO4, and concentrated in vacuo. The crude residue was distilled in order to purify the alcohol.
84 % ee
Stage #1: With dimethylsulfide borane complex; 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium hexafluorophosphate In tetrahydrofuran at 70℃; for 0.5 h; Inert atmosphere; Schlenk technique
Stage #2: With hydrogenchloride In waterInert atmosphere; Schlenk technique
General procedure: In a schlenk tube, BH3·SMe2(0.55 mmol, 275 L) was added inthe solution of IL 5 (28 mg, 10 molpercent) dissolved in THF (1 mL), undernitrogen atmosphere. The homogenous mixture was stirred andheated at 70C for 30 min. Later, a solution of ketone (0.5 mmolin THF (0.5 mL)) was added within 30 min. After the addition wascompleted, the solvent was evaporated under vacuum. An aqueoussolution of 1M HCl (5 mL) was added and the product was extractedwith DCM. The solvent was dried on anhydrous sodium sulfateand evaporated under reduced pressure. Crude residue was furtherpurified by column chromatography on silica gel using hexane-ethyl acetate as eluent. Enantiomeric excesses of all alcohols weredetermined by HPLC analysis using Chiralcel OD–H/AD–H chiralcolumn, isopropanol-n-hexane as mobile phase and HPLC condi-tions are given in SI.
46.8 % ee With seeds of Linum usitatissimum In aq. phosphate buffer at 25℃; for 72 h; Microbiological reaction General procedure: Studies were previously performed to determine the optimal reaction conditions among the parameters: amount ofbiocatalyst (2 g, 5 g, 10 g, and 20 g), time of reaction (24 h, 48, 72, and 96 h), use of co-solvent isopropyl alcohol in theproportions (v/v) 2, 5, and 10percent in distilled water and a buffer solution previously prepared from Na2HPO4–KH2PO4, withpH 6.0, 7.0, and 8.0, using 50 mg of acetophenone as pattern substrate. Therefore, the reactions were carried out in the bestreaction conditions among the parameters tested, using 50 mg of substrate and 20 g of biocatalyst in a buffer solution (Na2HPO4–KH2PO4), pH 6.0, over a period of 72 h at 25C without a co-solvent. In these reaction conditions, 70.4percent ofbioconversion and an ee of 93.7percent were obtained for pattern acetophenone. All biotransformation reactions were performedusing a modified methodology proposed by Machado et al. [11]. Whole seeds of Linum usitatissimum L. were washed with 5percentsodium hypochlorite and rinsed with sterile distilled water. Each individual carbonyl substrate, 1–14 (50 mg), was added to asuspension of 20 g of L. usitatissimum seeds in 40 mL of a buffered solution (Na2HPO4–KH2PO4), pH 6.0, and incubated at25C in an orbital shaker (175 rpm) for 72 h. Controls were similarly processed, except that no substrates were added. Allreactions were performed in triplicate. The course of all reactions was monitored by TLC (Merck, silica gel 60 F254) and thesubstances revealed by spraying with vanillin solution. After completion of the reaction, each suspension was filtered andwashed with water, and the aqueous solutions were extracted with CH2Cl2 (3 50 mL). The organic phases were dried withNa2SO4 and removed in a rotator evaporator. The reaction products were purified by column chromatography on silica gel60 VETEC with a binary mixture of hexane–ethyl acetate (8:2, v/v) as eluent to afford the (S)-alcohols (Scheme 1). The opticalrotations were measured on a PerkinElmer 241 digital polarimeter.
84 % ee With bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; formic acid; sodium formate; (1R,2R)-N1,N-di(naphthalen-1-yl)cyclohexane-1,2-diamine In methanol; water at 70℃; for 22 h; Inert atmosphere General procedure: In a pressure tube, 0.5 molpercent of metal precursor [C16H24BF4Ir](2.48 mg, 0.005 mol) and 1 molpercent of chiral amine ligand (3.66 mg,0.01 mmol) were dissolved in 2 mL of water and methanol (ratio1:1) and stirred at room temperature for 1 h under argon atmo-sphere. Then formic acid (2.5eq, 0.1 mL), sodium formate (2.5eq,170 mg) and 1eq of ketone substrate (1 mmol) were introduced.The reaction mixture was stirred at 500 rpm and heated at 70C for22 h. After that, the tube was cooled to room temperature; and theorganic compound was extracted with either with ethyl acetate orCH2Cl2, then the solution was dried over Na2SO4, filtrated and con-centrated under reduced pressure. The crude material was purifiedby flash column chromatography on silica gel using cyclohex-ane/ethyl acetate as gradient eluent (90:10–7:3). After evaporation,alcohols were obtained as oil or solid. The products were identifiedby NMR. The conversion and the enantioselectivity were deter-mined by chiral GC or chiral HPLC analysis (Scheme 1).
85 % ee at 20℃; for 1 h; Inert atmosphere General procedure: Ruthenium complex (3.7 mg, 0.004 mmol), ketone (2 mmol) andNaOiPr (0.4 mL, 0.1 M) were dissolved in degassed iPrOH (10 mL) and the mixture was stirred under nitrogen atmosphere at appropriate temperature. A small volume of sample was taken from reaction mixture and diluted with diethyl ether (1:1), and rapidly filtered using a short silica pad. The conversion and enantiomeric excess were determined by GC using Agilent HP-Chiral 20B column(30 m, 0.25 mm, 0.25 mm) and by HPLC using Supelco AD-H, OD-Hchiral columns.
87 % ee With C43H47ClFeIrN2P; potassium <i>tert</i>-butylate; hydrogen In ethanol at 20℃; for 16 h; Autoclave General procedure: (RC, SFe)-1-[2-(bis(3,5-dimethylphenyl)phosphino)ferrocenyl]N-(6-pyridyl-2-methyl)ethylamine (12.6 mg, 0.022 mmol), [Ir(COD)Cl2 (7.32 mg, 1 mmol)Was added to a 25 mL Schlenk reaction tube,Vacuum / nitrogen three times, 2 mL of anhydrous ethanol was purged with nitrogen, and the mixture was stirred at room temperature for 1 hour. Acetophenone (4.8 g, 40 mmol) was added to a 100 mL autoclave, Add 30 mLThe nitrogen-substituted absolute ethanol, Then, the reaction liquid is added into the reaction kettle,After replacing the hydrogen three times, the pressure was increased to 20 atm,The mixture was stirred at room temperature for 24 hours, TLC showed that the reaction was complete and the product was obtained as a pale yellow liquid (R)-1-phenylethanol 2.2 g in 90.9percent yield and 78percent ee.
56 % ee With C23H33ClN2O2RuS; potassium hydroxide In isopropyl alcohol at 40℃; for 48 h; General procedure: To a solution of ketone (0.55 mmol) in 2-propaol (0.5 mL) placed in a vial a 1 mL of 2-propanol solution of preformed ruthenium catalyst (11 μmol) and 0.1M KOH in 2-propanol solution (0.5 mL) were added. The mixture was stirred at 40 oC for 48 h. To reaction mixture 1 mL of water was added, neutralized with 10percent hydrochloric acid and extracted 3x4 mL of CH2Cl2. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue oil was purified with a column chromatography on silica gel using dichloromethane as eluent to afford appropriate ketone. The enantiomeric excess of alcohols was determined by HPLC analysis using a Chiracel OD-H column, hexane:i-PrOH (95:5 or 98:2), 1 mL/min. The enantiomeric excess of 1-(2-methylphenyl)ethanol and 1-(4-methylphenyl)ethanol were determined by comparison of the value and sign of specific rotation.
67 % ee With C23H33ClN2O2RuS; potassium hydroxide In isopropyl alcohol at 40℃; for 48 h; General procedure: To a solution of ketone (0.55 mmol) in 2-propaol (0.5 mL) placed in a vial a 1 mL of 2-propanol solution of preformed ruthenium catalyst (11 μmol) and 0.1M KOH in 2-propanol solution (0.5 mL) were added. The mixture was stirred at 40 oC for 48 h. To reaction mixture 1 mL of water was added, neutralized with 10percent hydrochloric acid and extracted 3x4 mL of CH2Cl2. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue oil was purified with a column chromatography on silica gel using dichloromethane as eluent to afford appropriate ketone. The enantiomeric excess of alcohols was determined by HPLC analysis using a Chiracel OD-H column, hexane:i-PrOH (95:5 or 98:2), 1 mL/min. The enantiomeric excess of 1-(2-methylphenyl)ethanol and 1-(4-methylphenyl)ethanol were determined by comparison of the value and sign of specific rotation.

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  • 5
  • [ 766-81-4 ]
  • [ 52780-14-0 ]
  • [ 134615-22-8 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6 h;
Stage #2: With C26H26ClN2O2RhS; water; sodium formate In methanol at 30℃; for 5 h;
A solution of 3-bromophenylacetylene (1 mmol), [(IPr) AuCl] (6.2 mg, 1 molpercent), methanol (1 ml) and water (0.5 ml) were successively added to a 25 ml Schlenk reaction flask. The mixture was reacted at 110 ° C for 6 hours and then cooled to room temperature.[Cp * RhCl [(R, R) -TsDPEN](1.7 mg, 0.003 mmol), water (1.5 ml) and sodium formate (340 mg, 5 equiv.) Were added to the reaction flask. The mixture was further reacted at 30 ° C for 5 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and then the title compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether) in 89percent yield, e.e.percent = 89percent
Reference: [1] Patent: CN106032347, 2016, A, . Location in patent: Paragraph 0058-0060
[2] Journal of Organic Chemistry, 2015, vol. 80, # 7, p. 3538 - 3546
  • 6
  • [ 108-05-4 ]
  • [ 52780-14-0 ]
  • [ 52780-14-0 ]
  • [ 134615-22-8 ]
  • [ 187844-70-8 ]
YieldReaction ConditionsOperation in experiment
73.2 % ee
Stage #1: With I287C mutant of Burkholderia cepacia NBRC 14595 lipase bearing an N-phenylacetamide (PAA) moiety immobilized on Toyonite 200M In di-isopropyl ether at 30℃; for 0.5 h; Molecular sieve; Resolution of racemate; Enzymatic reaction
Stage #2: at 30℃; for 9 h; Molecular sieve; Resolution of racemate; Enzymatic reaction
General procedure: A mixture of alcohol 1 (0.50 mmol), immobilized lipase (200 mg, 0.5percent(w/w) enzyme/Toyonite-200M), and molecular sieves 3A (three pieces) in dry i-Pr2O (5.0mL) in a test tube with a rubber septum was stirred at 30 °C for 30 min. The reaction wasstarted by addition of vinyl acetate (93 μL, 1.0 mmol) via a syringe. The progress of thereaction was monitored by TLC. The reaction was stopped by filtration at an appropriateconversion, and the filtrate was concentrated under reduced pressure. Alcohol 1 and ester 2were separated by silica gel column chromatography.
Reference: [1] Chemistry Letters, 2015, vol. 44, # 10, p. 1374 - 1376
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 12, p. 1418 - 1423
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YieldReaction ConditionsOperation in experiment
37 % ee
Stage #1: With I287C mutant of a Burkholderia cepacia lipase bearing an N-phenylacetamide (PAA) moiety In di-isopropyl ether at 30℃; for 0.5 h; Molecular sieve; Resolution of racemate; Enzymatic reaction
Stage #2: at 30℃; for 9 h; Molecular sieve; Resolution of racemate; Enzymatic reaction
General procedure: A mixture of alcohol 1 (0.50 mmol), immobilized lipase (200 mg, 0.5percent(w/w) enzyme/Toyonite-200M), and molecular sieves 3A (three pieces) in dry i-Pr2O (5.0mL) in a test tube with a rubber septum was stirred at 30 °C for 30 min. The reaction wasstarted by addition of vinyl acetate (93 μL, 1.0 mmol) via a syringe. The progress of thereaction was monitored by TLC. The reaction was stopped by filtration at an appropriateconversion, and the filtrate was concentrated under reduced pressure. Alcohol 1 and ester 2were separated by silica gel column chromatography.
Reference: [1] Chemistry Letters, 2015, vol. 44, # 10, p. 1374 - 1376
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 83, p. 23 - 28
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 8, p. 2085 - 2090[3] Angew. Chem., 2018, vol. 130, # 8, p. 2107 - 2112,6
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YieldReaction ConditionsOperation in experiment
87.8 - 88.1 % ee With N-ethyl-N,N-diisopropylamine In chloroform at 0℃; for 8.25 h; Resolution of racemate Procedure C. Variation of the substrate and the acylating agent in the CF3PIP-catalyzed kinetic resolutions. 1) The stock solution of the catalyst was prepared by dissolving 0.100 mmol of 2d (26.4 mg) and 3.75 mmol of N,N-diisopropylethylamine (6540L, 485 mg) in CHCl3 in a 5 mL volumetric flask and bringing the volume to the mark. 2) A one-dram vial was charged with 0.5 mmol of the racemic secondary alcohol and 0.500 mL of the stock solution of 2d, and cooled in an ice bath. After 15 minutes, 0.375 mmol of the anhydride was added. The mixture was swirled and left in the ice bath for a specified period of time, at the end of which it was quenched by rapid addition of 0.5 mL of methanol, allowed to warm slowly and left for one more hour at room temperature. The workup and chromatography were carried out as described in Procedure A.
Reference: [1] Patent: US2005/256150, 2005, A1, . Location in patent: Page/Page column 18
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  • [ 3132-99-8 ]
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 168 - 176
[2] European Journal of Organic Chemistry, 2012, # 9, p. 1703 - 1706
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Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 39, p. 12226 - 12227
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Reference: [1] European Journal of Organic Chemistry, 2013, # 4, p. 748 - 750
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 35, p. 10843 - 10846
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Reference: [1] Chemistry Letters, 2015, vol. 44, # 10, p. 1374 - 1376
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Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3250 - 3258
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Reference: [1] Green Chemistry, 2017, vol. 19, # 2, p. 474 - 480
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