p-benzyloxybenzaldehyde
4-fluoroaniline
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
In isopropyl alcohol at 40℃; | 95% |
In toluene Reflux; Large scale; | 93.6% |
In toluene for 48h; Heating; | 75% |
With magnesium sulfate In dichloromethane at 20℃; for 2h; |
benzyl bromide
4-hydroxy-benzaldehyde
4-fluoroaniline
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: benzyl bromide; 4-hydroxy-benzaldehyde With potassium carbonate at 20℃; for 12h; Stage #2: 4-fluoroaniline In acetone for 4h; Reflux; | 92% |
Stage #1: 4-hydroxy-benzaldehyde With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 0.25h; Stage #2: benzyl bromide In dichloromethane; water at 25 - 30℃; for 1.5h; Stage #3: 4-fluoroaniline In isopropyl alcohol at 20 - 60℃; for 2.5h; |
(S)-4-phenyl-2-oxazolidinone
B
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
4-hydroxy-benzaldehyde
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: isopropyl alcohol / 40 °C View Scheme |
benzyl chloride
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: isopropyl alcohol / 40 °C View Scheme |
N-(4-hydroxybenzylidene)-4-fluorobenzenamine
benzyl chloride
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 20.3 g |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
C40H36F2N2O5
Conditions | Yield |
---|---|
Stage #1: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5℃; for 2h; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 2h; Inert atmosphere; | 94% |
chloro-trimethyl-silane
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
Stage #1: chloro-trimethyl-silane; 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 5℃; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -5 - 5℃; for 1h; | 93% |
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In toluene at 60℃; | 88.94% |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
N-(4-(benzyloxy)benzyl)-4-fluoroaniline
Conditions | Yield |
---|---|
With 4-Fluorothiophenol In toluene for 8h; Sealed tube; Irradiation; | 85% |
3-{4-[2-(4-fluorophenyl)-5,5-dimethyl-[1,3]dioxin-2-yl]butyryl}(4S)-phenyl-1,3-oxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
3-{(2R,3S)-3-[(4-fluorophenyl)amino]-2-[2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]-3-[4-(benzyloxy)phenyI]propanoyl}-(4S)-4-phenyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -5℃; for 3h; | 78% |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: ethyl 3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propanoate; 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine With N-ethyl-N,N-diisopropylamine In dichloromethane at -30℃; for 0.166667h; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -30 - -20℃; for 3h; | 76% |
(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -50℃; for 0.5h; Stage #2: (-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one at -50℃; for 0.25h; Stage #3: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; DMF (N,N-dimethyl-formamide); hexane at -50℃; for 1h; | 67% |
(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: (-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -50℃; for 0.916667h; Stage #2: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine In tetrahydrofuran at -50℃; for 2.5h; Reagent/catalyst; | 67% |
(3S)-hydroxy-γ-butyrolactone
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
A
(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium chloride; lithium diisopropyl amide In tetrahydrofuran; N,N-dimethyl-formamide at -30 - -25℃; for 18h; Cycloaddition; | A 64% B n/a |
(4S)-N-acetyl-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl] imidazolidin-2-one With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Mannich Aminomethylation; Inert atmosphere; Stage #2: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine In tetrahydrofuran at -78 - 0℃; Mannich Aminomethylation; Inert atmosphere; stereoselective reaction; | 63% |
(S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -50℃; for 3.66667h; Inert atmosphere; | 62.5% |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - -20℃; for 5h; | 60.9% |
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(S)-3-{(R)-2-[(S)-[4-(benzyloxy)phenyl][(4-fluorophenyl)amino]methyl]-4-[2-(4-fluorophenyl)[1,3]dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one With titanium(IV) isopropylate; titanium tetrachloride In dichloromethane at 0℃; for 0.666667h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Stage #3: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine Product distribution / selectivity; | 58% |
5-(4-fluorophenyl)pentanoyl chloride
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
With tributyl-amine In toluene for 72h; Heating; | 48% |
1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 1h; Stage #2: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine In dichloromethane at -10℃; for 6h; optical yield given as %de; | 48% |
Stage #1: 1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Stage #2: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine In dichloromethane at -20℃; for 4h; Stage #3: With acetic acid In dichloromethane at -20 - 0℃; |
5,6-dihydro-pyran-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine With chloro(1,5-cyclooctadiene)rhodium(I) dimer; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 5,6-dihydro-pyran-2-one With diethylzinc In tetrahydrofuran; hexane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; | 46% |
5,6-dihydro-pyran-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; diethylzinc; aluminum isopropoxide In tetrahydrofuran at 20℃; for 24h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 9% |
pent-4-enoic acid
4-fluoro-1-iodobenzene
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Stage #1: pent-4-enoic acid; 4-fluoro-1-iodobenzene With tetrabutyl-ammonium chloride; potassium acetate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 80℃; Arylation; Stage #2: With oxalyl dichloride In dichloromethane at 22℃; for 1h; Substitution; Stage #3: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine With tributyl-amine In n-heptane; toluene at 80℃; for 18h; cyclocondensation; Staudinger conditions; |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 48 percent / tributylamine / toluene / 72 h / Heating 2: 63 percent / ammonium formate / 10 percent Pd/C / methanol / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: PPh3; KOAc; n-Bu4NCl / Pd(OAc)2 / dimethylformamide / 80 °C 1.2: oxalyl chloride / CH2Cl2 / 1 h / 22 °C 1.3: NBu3 / toluene; heptane / 18 h / 80 °C 2.1: 68 percent / BCl3*SMe2 / CH2Cl2 / 18 h / 20 °C 3.1: H2 / 10 percent Pd/C / ethyl acetate / 2 h / 760 Torr View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 48 percent / tributylamine / toluene / 72 h / Heating 2: 20 percent / ammonium formate / 10 percent Pd/C / methanol / Heating View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: PPh3; KOAc; n-Bu4NCl / Pd(OAc)2 / dimethylformamide / 80 °C 1.2: oxalyl chloride / CH2Cl2 / 1 h / 22 °C 1.3: NBu3 / toluene; heptane / 18 h / 80 °C 2.1: 68 percent / BCl3*SMe2 / CH2Cl2 / 18 h / 20 °C View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: PPh3; KOAc; n-Bu4NCl / Pd(OAc)2 / dimethylformamide / 80 °C 1.2: oxalyl chloride / CH2Cl2 / 1 h / 22 °C 1.3: NBu3 / toluene; heptane / 18 h / 80 °C 2.1: H2 / 10 percent Pd/C / ethyl acetate / 2 h / 760 Torr View Scheme | |
Multi-step reaction with 2 steps 1.1: PPh3; KOAc; n-Bu4NCl / Pd(OAc)2 / dimethylformamide / 80 °C 1.2: oxalyl chloride / CH2Cl2 / 1 h / 22 °C 1.3: NBu3 / toluene; heptane / 18 h / 80 °C 2.1: H2 / 10 percent Pd/C / ethyl acetate / 2 h / 760 Torr View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
[14C]-Sch 57871
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 3: formic acid / dichloromethane / 12 h / Reflux View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
ezetemibe
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr 6: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C View Scheme | |
Multi-step reaction with 7 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr 6: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C 7: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5 View Scheme | |
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 3: formic acid / dichloromethane / 12 h / Reflux 4: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C 5: acetic acid; ammonium formate; palladium 10% on activated carbon / 6 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 5 h / -30 - -20 °C 2.1: tetrabutyl ammonium fluoride / toluene / 3 h / 60 °C 3.1: sulfuric acid / isopropyl alcohol / 1 h / 20 °C 3.2: 2 h / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C 2: dimethylsulfide borane complex / dichloromethane; toluene / 3 h / -5 - 0 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 2 h View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr 6: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C View Scheme | |
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 3: formic acid / dichloromethane / 12 h / Reflux 4: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C View Scheme | |
Multi-step reaction with 2 steps 1: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C 2: dimethylsulfide borane complex / dichloromethane; toluene / 3 h / -5 - 0 °C / Inert atmosphere View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -30 °C / Inert atmosphere 1.2: 3 h / -30 - -20 °C 2.1: N,O-bis-(trimethylsilyl)-acetamide / dichloromethane / 3 h / 50 °C 2.2: 2 h / Reflux 3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -45 - 20 °C View Scheme |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C View Scheme |
The n-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, with the CAS register number 70627-52-0, has other names as 4-benzyloxybenzylidene-(4-fluoro)aniline; 4-(4-benzyloxybenzylidene)fluoroaniline; n-(4-(benzyloxy)benzylidene)-4-fluorobenzenamine; 4-fluoro-n-[[4-(phenylmethoxy)phenyl]methylene]benzenamine; n-(4-(benzyloxy)benzylidene)-4-fluoroaniline.
The physical characteristics could be summarized as: (1)ACD/LogP: 4.97; (2)#Hbondacceptors: 2; (3)#FreelyRotatingBonds: 5; (4)PolarSurfaceArea: 21.59; (5)IndexofRefraction: 1.558; (6)MolarRefractivity: 91.38cm3; (7)MolarVolume: 283cm3; (8)Polarizability: 36.22 ×10-24 cm3; (9)SurfaceTension: 37.6dyne/cm; (10)Density: 1.07g/cm3; (11)FlashPoint: 229.1°C; (12)EnthalpyofVaporization: 68.75kJ/mol; (13)BoilingPoint: 455.2°Cat760mmHg; (14)VapourPressure: 4.83E-08mmHgat25°C.
This is a kind of light yellow flaky crystal. As to its raw materials, they are including etanol, ethyl acetate, n,n-dimethylformamide, potassium carbonate, sodium sulfate, potassium iodide, benzyl bromide, petroleum ether, p-hydroxybenzaldehyde, 4-fluoroaniline. When store it, it should be kept sealing in low temperature. As to its usage, it is widely applied in many way, mainly in pharmaceutics, such as being used in the synthesis of cardiovascular drugs Ezetimibe.
In addition, you could refer to the following data information to get the molecular structure:
(1)SMILES:Fc3ccc(\N=C\c2ccc(OCc1ccccc1)cc2)cc3
(2)InChI:InChI=1/C20H16FNO/c21-18-8-10-19(11-9-18)22-14-16-6-12-20(13-7-16)23-15-17-4-2-1-3-5-17/h1-14H,15H2/b22-14+
(3)InChIKey:IWNBEFDVKWCBFY-HYARGMPZBF
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