Product Name

  • Name

    Atorvastatin tert-Butyl Ester

  • EINECS
  • CAS No. 134395-00-9
  • Article Data38
  • CAS DataBase
  • Density 1.16
  • Solubility
  • Melting Point 66-68ºC
  • Formula C37H43FN2O5
  • Boiling Point 721.0±60.0 °C(Predicted)
  • Molecular Weight 614.757
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 134395-00-9 (Atorvastatin tert-Butyl Ester)
  • Hazard Symbols
  • Synonyms 1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, 1,1-dimethylethyl ester, [R-(R*,R*)]-;(3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid tert-butyl ester;
  • PSA 100.79000
  • LogP 7.64370

Synthetic route

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate
125971-95-1

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
With hydrogenchloride; water In acetonitrile for 13h; Product distribution / selectivity;98.9%
With hydrogenchloride In methanol; water at 50 - 55℃;98%
With hydrogenchloride In methanol; water at 0 - 30℃; Industrial scale;96.7%
4-methyl-3-oxo-N-phenylpentanamide
124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: β-alanine; glacial acetic acid / hexane / Heating
2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
3: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
4: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
benzaldehyde
100-52-7

benzaldehyde

HI, I2

HI, I2

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: β-alanine; glacial acetic acid / hexane / Heating
2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
3: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
4: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide
125971-57-5

4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
2: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
3: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide
125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
2: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
2: aq. HCl / methanol
View Scheme
Multi-step reaction with 2 steps
1.1: cyclohexane / 0.5 h / 20 °C / Inert atmosphere; Large scale
1.2: Reflux; Large scale
2.1: hydrogenchloride / acetonitrile; water / 1.5 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: Trimethylacetic acid / toluene / 1 h / 105 - 110 °C / Industrial scale
2: hydrogenchloride / methanol; water / 0 - 30 °C / Industrial scale
View Scheme
aniline
62-53-3

aniline

Wang resin-bound styrene 4

Wang resin-bound styrene 4

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 96 percent / toluene / Heating
2: β-alanine; glacial acetic acid / hexane / Heating
3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
5: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
isobutyryl Meldrum's acid

isobutyryl Meldrum's acid

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 96 percent / toluene / Heating
2: β-alanine; glacial acetic acid / hexane / Heating
3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
5: HCl / tetrahydrofuran; H2O / 20 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2) NEt3 / 1) ethyl thiazolium catalyst / or with methyl thiazolium catalyst; 1) EtOH
2: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
3: aq. HCl / methanol
View Scheme
tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
125971-86-0, 125995-13-3

tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
2: aq. HCl / methanol
View Scheme
Multi-step reaction with 2 steps
1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
2: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: Acidic conditions
2: hydrogenchloride; methanol
View Scheme
2-((4R, 6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid tert-butyl ester
125971-94-0

2-((4R, 6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid tert-butyl ester

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / H2, ammonia / Molybdenum doped Raney nickel / methanol / 2585.7 Torr
2: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
3: aq. HCl / methanol
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; nickel; ammonia / methanol
2: Acidic conditions
3: hydrogenchloride; methanol
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; ammonia / cyclohexane; water / 30 - 40 °C / 3750.38 Torr / Autoclave
2: Trimethylacetic acid; diisopropylamine; tetra(n-butyl)ammonium hydrogensulfate / 40 h / 78 - 85 °C
3: hydrogenchloride; water / methanol / 25 - 30 °C
View Scheme
7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dioxo-heptanoic acid, tert-butyl ester

7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dioxo-heptanoic acid, tert-butyl ester

C37H43FN2O5

C37H43FN2O5

B

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
With formic acid; triethylamine; [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1,3,5-trimethylbenzene]-ruthenium In toluene for 24h;
C42H49FN2O5
1035204-85-3

C42H49FN2O5

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Stage #1: C42H49FN2O5 With hydrogenchloride In methanol; tert-butyl methyl ether; water at 50℃; for 5h;
Stage #2: With sodium hydroxide In methanol; tert-butyl methyl ether; water at 50℃; for 1h; pH=> 13; Product distribution / selectivity;
tert-butyl 2-((2R,4R)-4-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-1,5-dioxaspiro[5.5]undecan-2-yl)acetate
1035204-90-0

tert-butyl 2-((2R,4R)-4-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-1,5-dioxaspiro[5.5]undecan-2-yl)acetate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl 2-((2R,4R)-4-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-1,5-dioxaspiro[5.5]undecan-2-yl)acetate With hydrogenchloride In methanol; water for 18h; Heating / reflux;
Stage #2: With sodium hydroxide In methanol; tert-butyl methyl ether; water at 47 - 52℃; for 1h; Product distribution / selectivity;
tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate
125971-95-1

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate

A

atorvastatin lactone
125995-03-1

atorvastatin lactone

B

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
With hydroxylamine hydrochloride; water In methanol; acetone at 55 - 65℃; for 0.833333 - 1.25h; Product distribution / selectivity;
With hydrogenchloride; water In etanol; acetone at 55 - 65℃; for 0.833333 - 1.25h; Product distribution / selectivity;
5-(4-fluorophenyl)-2-(1-methylethyl)-1-(cis-t-butyl-2-ethoxy-3,5-dioxane-7-amido-heptanoate)-N,4-diphenyl-1H-pyrrole-3-carboxamide

5-(4-fluorophenyl)-2-(1-methylethyl)-1-(cis-t-butyl-2-ethoxy-3,5-dioxane-7-amido-heptanoate)-N,4-diphenyl-1H-pyrrole-3-carboxamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1.5h;
cis-t-butyl-7-nitro-3,5-dihydroxy-heptanoate
1370478-51-5

cis-t-butyl-7-nitro-3,5-dihydroxy-heptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: methanesulfonic acid / tetrahydrofuran / 0 °C
2: hydrogen; ammonia / palladium 10% on activated carbon / water; tetrahydrofuran; methanol / 6 h / 20 °C
3: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 0 °C / Inert atmosphere
5: acetic anhydride / 5 h / 75 - 80 °C / Inert atmosphere
6: hydrogenchloride; water / methanol / 1.5 h / 20 °C
View Scheme
cis-t-butyl-2-methoxy-3,5-dioxane-6-amino-(N-ethyl-(4-fluorobenzene)-acetate)-heptanoate

cis-t-butyl-2-methoxy-3,5-dioxane-6-amino-(N-ethyl-(4-fluorobenzene)-acetate)-heptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
2: acetic anhydride / 5 h / 75 - 80 °C / Inert atmosphere
3: hydrogenchloride; water / methanol / 1.5 h / 20 °C
View Scheme
cis-t-butyl-2-ethoxy-3,5-dioxane-6-amino(N,N-((4-fluorobenzene)isobutyryl)-acetic acid)-heptanoate

cis-t-butyl-2-ethoxy-3,5-dioxane-6-amino(N,N-((4-fluorobenzene)isobutyryl)-acetic acid)-heptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride / 5 h / 75 - 80 °C / Inert atmosphere
2: hydrogenchloride; water / methanol / 1.5 h / 20 °C
View Scheme
cis-t-butyl-2-methoxy-3,5-dioxane-7-nitro-heptanoate

cis-t-butyl-2-methoxy-3,5-dioxane-7-nitro-heptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogen; ammonia / palladium 10% on activated carbon / water; tetrahydrofuran; methanol / 6 h / 20 °C
2: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
3: triethylamine / dichloromethane / 0 °C / Inert atmosphere
4: acetic anhydride / 5 h / 75 - 80 °C / Inert atmosphere
5: hydrogenchloride; water / methanol / 1.5 h / 20 °C
View Scheme
cis-t-butyl-2-methoxy-3,5-dioxane-7-amino-heptanoate

cis-t-butyl-2-methoxy-3,5-dioxane-7-amino-heptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 0 °C / Inert atmosphere
3: acetic anhydride / 5 h / 75 - 80 °C / Inert atmosphere
4: hydrogenchloride; water / methanol / 1.5 h / 20 °C
View Scheme
5-(4-fluorophenyl)-2-(1-methylethyl)-1-(cis-t-butyl-2-ethoxy-3,5-dioxane-7-amido-heptanoate)-N-4-diphenyl-1H-pyrrole-3-carboxamide

5-(4-fluorophenyl)-2-(1-methylethyl)-1-(cis-t-butyl-2-ethoxy-3,5-dioxane-7-amido-heptanoate)-N-4-diphenyl-1H-pyrrole-3-carboxamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1.5h;
(R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide
1331869-16-9

(R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C
2.1: diethyl ether / 4.5 h / 0 - 20 °C
3.1: tetrahydrofuran; diethyl ether / -78 °C
3.2: -78 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
5.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
6.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
7.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
8.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
9.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
10.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
11.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
12.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
(R)-N,N-diallyl-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentanethioamide
1347738-07-1

(R)-N,N-diallyl-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentanethioamide

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: diethyl ether / 4.5 h / 0 - 20 °C
2.1: tetrahydrofuran; diethyl ether / -78 °C
2.2: -78 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
4.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
5.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
6.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
7.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
8.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
9.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
10.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
11.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
CF3O3S(1-)*C25H42NO2SSi(1+)

CF3O3S(1-)*C25H42NO2SSi(1+)

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: tetrahydrofuran; diethyl ether / -78 °C
1.2: -78 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
3.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
4.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
5.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
6.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
7.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
8.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
9.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
10.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
(R)-tert-butyl 7-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-3-oxoheptanoate
1331869-20-5

(R)-tert-butyl 7-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-3-oxoheptanoate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
2: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
3: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
4: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
5: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
6: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
7: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
8: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
9: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
C18H26O5

C18H26O5

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
2: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
3: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
4: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
6: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
7: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
8: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
C18H28O5

C18H28O5

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
2: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
3: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
4: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
5: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
6: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
7: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
tert-butyl 2-((4R,6R)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
1331869-21-6

tert-butyl 2-((4R,6R)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
2: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
3: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
4: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
5: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
6: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
tert-butyl 2-((4R,6R)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
1173184-84-3

tert-butyl 2-((4R,6R)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
2: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
3: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
4: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
5: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
View Scheme
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin hemicalcium salt trihydrate

atorvastatin hemicalcium salt trihydrate

Conditions
ConditionsYield
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With sodium hydroxide In acetonitrile at 45 - 60℃; for 3h;
Stage #2: With water In acetonitrile at 45 - 60℃;
Stage #3: With calcium(II) nitrate for 4.5h; Reagent/catalyst; Solvent;		99.62%
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin sodium
134523-01-6

atorvastatin sodium

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane; tert-butyl methyl ether for 21h; Product distribution / selectivity; Heating / reflux;97.7%
With methanol; sodium hydroxide; water In tert-butyl methyl ether for 21h; Product distribution / selectivity; Heating / reflux;91%
With sodium hydroxide; water; tert-butyl alcohol In tert-butyl methyl ether for 21h; Product distribution / selectivity; Heating / reflux;91%
L-arginine
74-79-3

L-arginine

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin arginine

atorvastatin arginine

Conditions
ConditionsYield
In methanol for 8h; Reflux;72.9%
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin
134523-00-5

atorvastatin

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; Hydrolysis;
With methanol; potassium hydroxide; water
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With methanol; sodium hydroxide; water In tert-butyl methyl ether for 2.08333 - 7.08333h; Heating / reflux;
Stage #2: With hydrogenchloride pH=8.0 - 8.2;
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

lipitor
134523-03-8

lipitor

Conditions
ConditionsYield
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With sodium hydroxide In methanol; water at 50℃; for 1h;
Stage #2: With calcium acetate In water; ethyl acetate at 50℃; for 1h;
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With sodium hydroxide; water In acetonitrile at 40 - 45℃; for 2h;
Stage #2: With calcium acetate In water; acetonitrile at 40 - 45℃; for 0.5 - 1h;
Stage #3: With sodium hydroxide In water; acetonitrile at 70 - 80℃; for 7 - 9h;
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With sodium hydroxide In methanol; water
Stage #2: With calcium chloride In water at 55 - 60℃; Product distribution / selectivity;
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

[R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid; ammonium salt
340266-37-7

[R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid; ammonium salt

Conditions
ConditionsYield
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With methanol; sodium hydroxide; water at 55℃; for 2.5h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether (MTBE); water at 20℃;
Stage #3: With ammonia In tert-butyl methyl ether; water for 2 - 3h; Product distribution / selectivity;
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

[R-(R*,R*)]2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid sodium salt

[R-(R*,R*)]2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid sodium salt

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 45 - 50℃; for 5 - 6h;
atorvastatin lactone
125995-03-1

atorvastatin lactone

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin sodium
134523-01-6

atorvastatin sodium

Conditions
ConditionsYield
With sodium hydroxide; water In methanol at 35 - 45℃; for 0.5 - 0.666667h; Product distribution / selectivity;
With sodium hydroxide; water In ethanol at 35 - 45℃; for 0.5 - 0.666667h; Product distribution / selectivity;
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin lactone
125995-03-1

atorvastatin lactone

Conditions
ConditionsYield
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With potassium hydroxide
Stage #2: With hydrogenchloride In water
Stage #3: With toluene-4-sulfonic acid In toluene Reflux;
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester
134395-00-9

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

atorvastatin hemicalcium

atorvastatin hemicalcium

Conditions
ConditionsYield
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With water; sodium hydroxide In methanol; tert-butyl methyl ether Inert atmosphere; Reflux;
Stage #2: With calcium chloride hexahydrate In water at 20 - 25℃; Inert atmosphere;

Atorvastatin tert-Butyl Ester Chemical Properties

Synonyms: 7-[2-(4-Fluoro-phenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5- dihydroxy-heptanoic Acid tert-Butyl Ester ; Atorvastatin tert-Butyl Ester ; (R,dR)-2-(4-Fluorophenyl)-,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic Acid 1,1-Dimethylethyl Ester 
Product Name: Atorvastatin tert-Butyl Ester
CAS: 134395-00-9
Melting point: 66-68°C
Empirical Formula:: C37H43FN2O5
Product Categories: Chiral Reagents; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals

Atorvastatin tert-Butyl Ester Specification

  Atorvastatin tert-Butyl Ester (CAS NO.134395-00-9) is an off-white to pale yellow solid, it is an impurity arising in the synthesis of Atorvastatin.

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