Product Name

  • Name

    tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate

  • EINECS 258-925-2
  • CAS No. 125971-95-1
  • Article Data45
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility
  • Melting Point 144-148 °C
  • Formula C40H47FN2O5
  • Boiling Point 678.035 °C at 760 mmHg
  • Molecular Weight 654.822
  • Flash Point 363.863 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 125971-95-1 (tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate)
  • Hazard Symbols
  • Synonyms 1,3-Dioxane-4-aceticacid,6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-,1,1-dimethylethyl ester, (4R-cis)-;(4R-cis)-1,1-dimethylethyl-6-[2-[2-(4-fluorophenyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate(L-1);1,3-Dioxane-4-aceticacid,6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-,1,1-dimethylethyl ester, (4R,6R)-;
  • PSA 78.79000
  • LogP 9.44200

Synthetic route

C40H45FN2O5

C40H45FN2O5

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen97%
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

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

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

Conditions
ConditionsYield
With Trimethylacetic acid In toluene at 105 - 110℃; for 1h; Industrial scale;96.5%
With tetra(n-butyl)ammonium hydrogensulfate; diisopropylamine; Trimethylacetic acid at 78 - 85℃; for 40h; Paal-Knorr Pyrrole Synthesis;82.3%
With Trimethylacetic acid In tetrahydrofuran; n-heptane; toluene Heating;75%
C26H22FNO3
1331869-19-2

C26H22FNO3

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

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

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylacetic acid In cyclohexane at 80 - 84℃; for 25h; Concentration; Reagent/catalyst; Paal-Knorr Pyrrole Synthesis; Dean-Stark; Reflux;79%
With Trimethylacetic acid In tetrahydrofuran; hexane; toluene at 110℃; for 30h; Paal-Knorr pyrrole synthesis; Inert atmosphere;
tert-butyl 2-((4R,6S)-6-(2-iodoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
1173184-80-9

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

5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide

5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide

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

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetonitrile Reflux;65%
t-butyl 2-((4R,6R)-6-(2-(2-isopropyl-4-phenyl-3-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

t-butyl 2-((4R,6R)-6-(2-(2-isopropyl-4-phenyl-3-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

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

Conditions
ConditionsYield
With potassium acetate; palladium diacetate at 150℃; for 15h; Heck Reaction; Inert atmosphere;44%
4-methyl-3-oxo-N-phenylpentanamide
124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

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

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
Multi-step reaction with 3 steps
1.1: L-proline / Inert atmosphere
2.1: 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide; potassium phosphate / acetonitrile / 16 h / 120 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
2.2: 4 h / 120 °C / Inert atmosphere; Gas phase; Schlenk technique; Sealed tube
3.1: potassium acetate; palladium diacetate / 15 h / 150 °C / Inert atmosphere
View Scheme
benzaldehyde
100-52-7

benzaldehyde

HI, I2

HI, I2

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

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide
125971-57-5

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
2: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide; potassium phosphate / acetonitrile / 16 h / 120 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
1.2: 4 h / 120 °C / Inert atmosphere; Gas phase; Schlenk technique; Sealed tube
2.1: potassium acetate; palladium diacetate / 15 h / 150 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / Reflux
2: Trimethylacetic acid / toluene; hexane; tetrahydrofuran / Reflux
View Scheme
aniline
62-53-3

aniline

Wang resin-bound styrene 4

Wang resin-bound styrene 4

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

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
isobutyryl Meldrum's acid

isobutyryl Meldrum's acid

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

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2) NEt3 / 1) ethyl thiazolium catalyst / or with methyl thiazolium catalyst; 1) EtOH
2: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
View Scheme
Multi-step reaction with 2 steps
1: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / Reflux
2: Trimethylacetic acid / toluene; hexane; tetrahydrofuran / Reflux
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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / H2, ammonia / Molybdenum doped Raney nickel / methanol / 2585.7 Torr
2: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; nickel; ammonia / methanol
2: Acidic conditions
View Scheme
Multi-step reaction with 2 steps
1: ammonia; hydrogen / methanol / 6 h / 30 - 40 °C / 2250.23 - 3000.3 Torr / Autoclave
2: Trimethylacetic acid / tetrahydrofuran; n-heptane / 60 h / Reflux
View Scheme
Multi-step reaction with 2 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
View Scheme
1-[2-((4R,6R)-6-tert-butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)ethyl]-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid
805242-36-8

1-[2-((4R,6R)-6-tert-butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)ethyl]-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid

aniline
62-53-3

aniline

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

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 50 - 60℃; Product distribution / selectivity;
C34H41ClFNO5

C34H41ClFNO5

aniline
62-53-3

aniline

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

Conditions
ConditionsYield
In benzene at 70℃; Product distribution / selectivity;
C39H50FNO8

C39H50FNO8

aniline
62-53-3

aniline

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran at 55 - 60℃; Product distribution / selectivity;
4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide

4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide

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

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

Conditions
ConditionsYield
With 2-Methylbutanoic acid In n-heptane; toluene for 22h; Product distribution / selectivity; Heating / reflux;
With Trimethylacetic acid In n-heptane; toluene for 25h; Heating / reflux;
With 2-Methylbutanoic acid In n-heptane; toluene for 48h; Product distribution / selectivity; Heating / reflux;
2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]-4-methyl-N-methyl-N-phenyl-3-oxo-pentanamide

2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]-4-methyl-N-methyl-N-phenyl-3-oxo-pentanamide

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

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

Conditions
ConditionsYield
In tetrahydrofuran; n-heptane; oenanthic acid; toluene for 8h; Heating / reflux;
(4R-cis)-1,1-dimethylethyl-[6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate
914222-70-1

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

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

isopropyl alcohol
67-63-0

isopropyl alcohol

A

(4R-cis)-1,1-dimethylethyl 6-[2]2-(-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl ]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate

(4R-cis)-1,1-dimethylethyl 6-[2]2-(-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl ]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate

B

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

Conditions
ConditionsYield
In n-heptane; toluene
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

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

isopropyl alcohol
67-63-0

isopropyl alcohol

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

Conditions
ConditionsYield
In n-heptane; toluene
tert-butyl [(4S,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate
1105067-89-7

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

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

A

tert-butyl (4S,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate
1105067-90-0

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

B

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

Conditions
ConditionsYield
With Trimethylacetic acid In n-heptane; toluene for 19h; Heating; Title compound not separated from byproducts.;
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

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

A

((4R,6R)-6-{2-[2-((4R,6R)-6-{2-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetylamino]-ethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid tert-butyl ester
1116118-82-1

((4R,6R)-6-{2-[2-((4R,6R)-6-{2-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetylamino]-ethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid tert-butyl ester

B

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

Conditions
ConditionsYield
Stage #1: tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide In toluene at 90 - 100℃; for 1 - 1.5h; Heating / reflux;
Stage #2: Trimethylacetic acid In toluene Product distribution / selectivity; Heating / reflux;
Stage #1: tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide In tetrahydrofuran; n-heptane; toluene at 40 - 50℃; for 1 - 1.5h; Heating / reflux;
Stage #2: Trimethylacetic acid In tetrahydrofuran; n-heptane; toluene for 35h; Product distribution / selectivity; Heating / reflux;
Stage #1: tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide In tetrahydrofuran; toluene at 40 - 50℃; for 1 - 1.5h; Heating / reflux;
Stage #2: Trimethylacetic acid In tetrahydrofuran; toluene for 24h; Product distribution / selectivity; Heating / reflux;
+/-(4-fluoro-alpha-(2-methyl-1-oxopropyl)-gama-oxo-N-beta-diphenyl benzenebutaneamine)

+/-(4-fluoro-alpha-(2-methyl-1-oxopropyl)-gama-oxo-N-beta-diphenyl benzenebutaneamine)

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

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

Conditions
ConditionsYield
Stage #1: +/-(4-fluoro-alpha-(2-methyl-1-oxopropyl)-gama-oxo-N-beta-diphenyl benzenebutaneamine); tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate With Trimethylacetic acid In tetrahydrofuran; n-heptane; toluene for 40 - 50h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; n-heptane; water; toluene pH=7; Product distribution / selectivity;
Stage #1: +/-(4-fluoro-alpha-(2-methyl-1-oxopropyl)-gama-oxo-N-beta-diphenyl benzenebutaneamine); tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate With Trimethylacetic acid In tetrahydrofuran; hexane; toluene for 40 - 50h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; hexane; water; toluene pH=7; Product distribution / selectivity;
(R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide
1331869-16-9

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

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

Conditions
ConditionsYield
Multi-step reaction with 11 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
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

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

Conditions
ConditionsYield
Multi-step reaction with 10 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
View Scheme
CF3O3S(1-)*C25H42NO2SSi(1+)

CF3O3S(1-)*C25H42NO2SSi(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
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

Conditions
ConditionsYield
Multi-step reaction with 9 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
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

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

Conditions
ConditionsYield
Multi-step reaction with 8 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
View Scheme
C18H26O5

C18H26O5

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

Conditions
ConditionsYield
Multi-step reaction with 7 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
View Scheme
C18H28O5

C18H28O5

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

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
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%
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

lipitor
134523-03-8

lipitor

Conditions
ConditionsYield
Stage #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 With hydrogenchloride; methanol; water at 35℃; for 3h;
Stage #2: With calcium hydroxide In methanol; water; toluene at 70℃; for 2h;
Stage #3: In methanol; water at 20 - 78℃; for 24.25h;
96%
Stage #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 With hydrogenchloride; water In methanol at 15 - 30℃; for 12h;
Stage #2: With sodium hydroxide In methanol; water at 25 - 30℃; for 6h; pH=12;
Stage #3: With hydrogenchloride; calcium acetate Product distribution / selectivity; more than 3 stages;
93.94%
Stage #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 With hydrogenchloride; water In methanol at 15 - 30℃; for 10 - 12h;
Stage #2: With sodium hydroxide In methanol; water at 25 - 30℃; for 4 - 6h; pH=~ 12;
Stage #3: With hydrogenchloride; calcium acetate Product distribution / selectivity; more than 3 stages;
86.5%
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

[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: 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 With hydrogenchloride In methanol; water at 50℃; for 10h;
Stage #2: With methanol; sodium hydroxide; water at 20 - 60℃; for 10h;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
95%
methanol
67-56-1

methanol

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

methyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
1353049-81-6

methyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Conditions
ConditionsYield
With sodium hydroxide for 7h; Reflux;37%
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

atorvastatin
134523-00-5

atorvastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / tetrahydrofuran; H2O / 20 °C
2: sodium hydroxide / H2O; tetrahydrofuran / 20 °C
View Scheme
Stage #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 With hydrogenchloride; water In tetrahydrofuran; methanol at 20℃;
Stage #2: With sodium hydroxide; water In tetrahydrofuran; methanol at 0 - 20℃;
Stage #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 With hydrogenchloride; water In tetrahydrofuran at 25℃; for 8h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran for 8h;
Stage #3: With phosphoric acid In water; ethyl acetate pH=4.0; 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

atorvastatin sodium
134523-01-6

atorvastatin sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / methanol
2: aq. NaOH / methanol
View Scheme
Stage #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 With hydroxylamine hydrochloride In methanol; water; acetone at 55 - 65℃; Industry scale;
Stage #2: With sodium hydroxide In methanol; water at 35 - 45℃; Product distribution / selectivity;
Stage #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 With hydrogenchloride; water In tetrahydrofuran at 25℃; for 6.25h; Industry scale;
Stage #2: With sodium hydroxide In tetrahydrofuran at 31℃; for 14h; Product distribution / selectivity; Cooling;
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

C34H35FN2O3

C34H35FN2O3

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol; water; acetone at 67℃; for 1h; Product distribution / selectivity; Heating / reflux;
With hydroxylamine hydrochloride In water; isopropyl alcohol; acetone at 67℃; for 1h; Product distribution / selectivity; Heating / reflux;
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

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

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

Conditions
ConditionsYield
Stage #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 With hydrogenchloride In methanol; water at 20 - 26℃; for 6.25h;
Stage #2: With sodium hydroxide In methanol; water at 25 - 30℃; for 6h; pH=~ 12;
Stage #3: With hydrogenchloride; magnesium acetate In methanol; water at 20 - 55℃; pH=7.8 - 8;
Stage #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 With hydrogenchloride; methanol; water at 20 - 25℃; for 3.75h;
Stage #2: With sodium hydroxide In methanol; water at 20 - 25℃; for 3h;
Stage #3: With hydrogenchloride; magnesium acetate more than 3 stages;

tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate Chemical Properties

The Molecular Structure of tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate (CAS NO.125971-95-1):

Empirical Formula: C40H47FN2O5
Molecular Weight: 654.81 
Appearance: White Solid
Product Categories: (intermediate of atorvastatin);Chiral Reagents;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules
Nominal Mass: 654 Da
Average Mass: 654.81 Da
Monoisotopic Mass: 654.346901 Da 
Index of Refraction: 1.569
Molar Refractivity: 186.677 cm3
Molar Volume: 569.569 cm3 
Surface Tension: 39.163 dyne/cm
Density: 1.15 g/cm3
Flash Point: 363.863 °C
Enthalpy of Vaporization: 99.525 kJ/mol
Boiling Point: 678.035 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C 
Melting point: 144-148 °C

tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate Uses

  tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate (CAS NO.125971-95-1) is used as intermediate of atorvastatin.

tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate Safety Profile

WGK Germany: 3

tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate Specification

 tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate (CAS NO.125971-95-1) is also called as (4R,6R)-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-Dioxane-4-acetic acid 1,1-dimethylethyl ester .

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