Product Name

  • Name

    Ezetimibe

  • EINECS 682-606-0
  • CAS No. 163222-33-1
  • Article Data70
  • CAS DataBase
  • Density 1.334 g/cm3
  • Solubility
  • Melting Point 164-166 °C
  • Formula C24H21F2NO3
  • Boiling Point 654.9 °C at 760 mmHg
  • Molecular Weight 409.432
  • Flash Point 349.9 °C
  • Transport Information
  • Appearance white powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 163222-33-1 (Ezetimibe)
  • Hazard Symbols R36/37/38:;
  • Synonyms (-)-Sch 58235;Zetia (TN);Zetia;Ezetimibe 1-(4-flurophenyl)-(3R)-[3-(4-flurophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone;2-Azetidinone,1-(4-fluorophenyl)-3-[(3S)-3- (4-fluorophenyl)-3-hydroxypropyl]-4-(4- hydroxyphenyl)-,(3R,4S)-;Sch 58235;Vytorin;Ezedoc;(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone;
  • PSA 60.77000
  • LogP 4.95330

Synthetic route

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; cyclohexane at 70℃; under 760.051 Torr; for 3h;99%
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50 - 55℃; under 37.5038 - 75.0075 Torr;90.3%
With palladium 10% on activated carbon; ammonium formate; acetic acid for 6h; Reflux;90%
1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone hydrate
873205-85-7

1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone hydrate

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
In n-heptane; tert-butyl methyl ether at 20℃; Product distribution / selectivity; Heating / reflux;99%
In Isopropyl acetate at 20℃; Product distribution / selectivity; Heating / reflux;
With acetic acid at 20℃; Product distribution / selectivity; Heating / reflux;
(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone

(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With sulfuric acid In water; isopropyl alcohol at 20 - 25℃; for 1h;95%
With perchloric acid at 40℃; for 3h; Temperature; Solvent;92%
With sulfuric acid In water; isopropyl alcohol at 20℃; for 1h;91.5%
C30H35F2NO3Si

C30H35F2NO3Si

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With pyridine hydrofluoride In tetrahydrofuran; pyridine at 20℃; for 24h;93%
4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl pivalate
1232148-26-3

4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl pivalate

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Stage #1: 4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl pivalate With sodium hydroxide In tetrahydrofuran; methanol at -15℃;
Stage #2: With hydrogenchloride; water In ethyl acetate		92%
C39H45ClF2N2O5Si2

C39H45ClF2N2O5Si2

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In tert-butyl methyl ether at 20℃; for 0.25h;91%
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With dimethylsulfide borane complex; trifluoroacetic anhydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -25 - -20℃; for 3h; Inert atmosphere;90%
With glucose dehydrogenase; alpha-D-glucopyranose; NADP; KRED-128 In water; isopropyl alcohol at 35℃; for 1.5h; pH=7; Product distribution / selectivity; Phosphate buffer;89.26%
With glucose dehydrogenase; potassium phosphate; alpha-D-glucopyranose; DL-dithiothreitol; NADP; magnesium sulfate; KRED-118 In methanol; water at 30℃; pH=7.0; Product distribution / selectivity;87.59%
C28H29F2NO5

C28H29F2NO5

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With hydrogen bromide In isopropyl alcohol at 20℃; for 4h;87%
(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-2-one
1004520-48-2

(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid at 20℃; for 2h; Time;86.23%
With dihydrogen peroxide In water; isopropyl alcohol at 20℃; for 0.5h;
(3R,4S)-1-(4-fluorophenyl)-[3(S)-hydroxy-3-(4-fluorophenyl)propyl]-[4-(phenylmethoxy)phenyl]-2-azetidinone

(3R,4S)-1-(4-fluorophenyl)-[3(S)-hydroxy-3-(4-fluorophenyl)propyl]-[4-(phenylmethoxy)phenyl]-2-azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid In ethanol at 25℃; for 4h; pH=3;85.4%
C36H49F2NO3Si2

C36H49F2NO3Si2

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With hydrogen fluoride In ethanol at 0 - 10℃; Inert atmosphere;80.6%
benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate
1159183-24-0

benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 23h; Product distribution / selectivity;76%
C42H61F2NO3Si2

C42H61F2NO3Si2

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With trimethyl(benzyl)ammonium fluoride In propan-1-ol at 20 - 30℃; Inert atmosphere;75.1%
C34H35F2NO3Si

C34H35F2NO3Si

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Stage #1: C34H35F2NO3Si With sulfuric acid In isopropyl alcohol at 20℃; for 1h;
Stage #2: With palladium 10% on activated carbon; hydrogen; ammonium formate In methanol for 2h; Inert atmosphere;		75%
C43H35F2NO3
1042722-68-8

C43H35F2NO3

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With hydrogen; 3% Pd/C In methanol at 20℃; for 18h; Product distribution / selectivity;73.3%
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

A

ezetemibe
163222-33-1

ezetemibe

B

(3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one
163380-16-3

(3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; dichloromethane; toluene at -8 - 0℃; for 4h; Corey-Bakshi-Shibata Reduction; Inert atmosphere; stereoselective reaction;A 55.4%
B n/a
With hydrogen; palladium 10% on activated carbon In ethanol under 3102.97 Torr; for 16h;
With Rhodococcus fascians MO22 cells at 35℃; pH=7; Microbiological reaction; aq. phosphate buffer; optical yield given as %de; diastereoselective reaction;
(3R,4S)-4-(4-(trimethylsilyloxy)phenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
954109-26-3

(3R,4S)-4-(4-(trimethylsilyloxy)phenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Stage #1: (3R,4S)-4-(4-(trimethylsilyloxy)phenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; methanol; toluene at -25 - 25℃; for 2.5 - 2.75h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; methanol; toluene at 0℃; for 0.5h; Product distribution / selectivity;
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

A

(3R,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one

(3R,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one

B

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With formic acid; triethylamine; (1S,2S)-N-methanesulfonyl-1,2-diphenylethane-1,2-diamine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tert-butyl methyl ether at 65℃; for 17h; Product distribution / selectivity;A n/a
B n/a
With formic acid; triethylamine; dichloro(benzene)ruthenium(II) dimer; (1S,2S)-N-methanesulfonyl-1,2-diphenylethane-1,2-diamine In tert-butyl methyl ether at 65℃; for 17h; Product distribution / selectivity;A n/a
B n/a
With formic acid; triethylamine; dichloro(mesitylene)ruthenium(II) dimer; N-((1S,2S)-2-amino-1,2-diphenylethyl)-1,1,1-trifluoromethanesulfonamide In tert-butyl methyl ether at 65℃; for 17h; Product distribution / selectivity;A n/a
B n/a
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
2: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
Multi-step reaction with 2 steps
1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
View Scheme
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; tetrahydrofuran / 5 h / 0 °C
2: palladium on activated charcoal; hydrogen / methanol / 6 h / 20 °C / 3800.26 Torr
View Scheme
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; dichloromethane / 5 h / 0 °C
2: palladium on activated charcoal; hydrogen / methanol / 6 h / 20 °C / 3800.26 Torr
View Scheme
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / -10 °C / Inert atmosphere
2: palladium on activated charcoal; formic acid; ammonium formate / isopropyl alcohol / 3 h / 40 °C
View Scheme
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
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
(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde
221349-58-2

(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr
4: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C
View Scheme
Multi-step reaction with 5 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
5: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one
221349-56-0

(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
2: BF3 etherate / toluene / 0.08 h / -30 °C
3: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
4: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr
5: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
2: BF3 etherate / toluene / 0.08 h / -30 °C
3: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
4: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
5: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
6: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
lithium; 1-(4-fluoro-phenyl)-ethenolate

lithium; 1-(4-fluoro-phenyl)-ethenolate

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr
4: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C
View Scheme
Multi-step reaction with 5 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
5: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one
221349-60-6

(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr
2: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C
View Scheme
Multi-step reaction with 3 steps
1: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
2: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
3: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one
231301-00-1

(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
2: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr
3: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C
View Scheme
Multi-step reaction with 4 steps
1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
2: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
3: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
4: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5
View Scheme
(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine
219653-96-0

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: (nBu)3N / heptane; toluene / 80 - 90 °C
2: LiOH*H2O / methanol / 2 h
3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
5: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
6: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
3: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
4: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
View Scheme
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
204589-84-4

3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
2: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
3: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
View Scheme
methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
204589-80-0

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LiOH*H2O / methanol / 2 h
2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
4: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
5: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: diethyl aluminiumcholoride / toluene / -12 - 20 °C / Inert atmosphere
2.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere
2.2: 1 h / -5 - 0 °C
3.1: [(S,S)-teth-TsDpen RuCl]; triethylamine; formic acid / ethylbenzene / 24 h / 35 - 40 °C / Inert atmosphere
4.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 50 - 55 °C / 37.5 - 75.01 Torr
View Scheme
acetic anhydride
108-24-7

acetic anhydride

ezetemibe
163222-33-1

ezetemibe

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone
163380-20-9

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane100%
With dmap; triethylamine In dichloromethane at 20℃; for 2h;96%
phenyl trifluoromethanesulfonamide
456-64-4

phenyl trifluoromethanesulfonamide

ezetemibe
163222-33-1

ezetemibe

(trifluoromethanesulfonyl)ezetimibe
847781-45-7

(trifluoromethanesulfonyl)ezetimibe

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 3.5h;99%
With dmap; triethylamine In dichloromethane at 20℃; for 3.5h;96%
benzyl bromide
100-39-0

benzyl bromide

ezetemibe
163222-33-1

ezetemibe

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;99%
acetic anhydride
108-24-7

acetic anhydride

ezetemibe
163222-33-1

ezetemibe

Acetic acid 4-{(2S,3R)-1-(4-fluoro-phenyl)-3-[(S)-3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenyl ester
795306-53-5

Acetic acid 4-{(2S,3R)-1-(4-fluoro-phenyl)-3-[(S)-3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenyl ester

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol for 5h;97%
With sodium hydroxide In water; isopropyl alcohol for 5h;97%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

ezetemibe
163222-33-1

ezetemibe

3-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(4-fluoro-phenyl)-azetidin-2-one
849799-39-9

3-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(4-fluoro-phenyl)-azetidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 5h;97%
With 1H-imidazole In DMF (N,N-dimethyl-formamide) for 5h;97%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

ezetemibe
163222-33-1

ezetemibe

(trifluoromethanesulfonyl)ezetimibe
847781-45-7

(trifluoromethanesulfonyl)ezetimibe

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 3.5h;96%
With dmap; triethylamine In dichloromethane at 23℃; for 3h;95%
With dmap; triethylamine In dichloromethane at 23℃; for 3h;95%
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;562.7 mg
benzyl chloroformate
501-53-1

benzyl chloroformate

ezetemibe
163222-33-1

ezetemibe

benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate
1159183-24-0

benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.5h;92%

Ezetimibe Chemical Properties

Name: Ezetimibe
Synonyms: 1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one
CAS Registry Number: 163222-33-1
Molecular Formula: C24H21F2NO3
Molecular Weight: 409.43
Molecular Structure:
Mp: 164-166°C

Ezetimibe Uses

Ezetimibe is an anti-hyperlipidemic medication which is used to lower Cholesterol levels. It acts by decreasing Cholesterol absorption in the intestine. It could be used alone when other Cholesterol-lowering medications are not tolerated, or when Cholesterol levels are unable to be controlled on statins alone, ezetimibe could be used together with statins

Ezetimibe Safety Profile

Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
Use cautiously in:
1)breastfeeding patients
2)children younger than age 10
3)pregnant patients not receiving HMG-CoA reductase inhibitors
4)renal or hepatic impairment
5)elderly patients.

Ezetimibe Specification

Patient monitoring:
1)Monitor hepatic and lipid profiles
2)Assess for and report unexplained muscle pain.

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