Abiraterone supplier | CasNO.154229-19-3

Name
Abiraterone
EINECS 810-941-6
CAS No. 154229-19-3
Article Data46
CAS DataBase
Density 1.14 g/cm³
Solubility
Melting Point 227-228 °C(Solv: toluene (108-88-3))
Formula C₂₄H₃₁NO
Boiling Point 500.17 °C at 760 mmHg
Molecular Weight 349.516
Flash Point 256.294 °C
Transport Information
Appearance white solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 17-(3-Pyridyl)androsta-5,16-dien-3beta-ol;CB 7598;Androsta-5,16-dien-3-ol,17-(3-pyridinyl)-, (3b)-;
PSA 33.12000
LogP 5.39860

Synthetic route

: 154229-18-2
abiraterone acetate

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 0 - 20℃; for 48h; Inert atmosphere;	99%
With lithium hydroxide In tetrahydrofuran; methanol; water for 1h;	96%
With sodium hydroxide In methanol at 20℃; for 2h; Reagent/catalyst;	95.8%

: C27H39NOSi

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 30℃; for 1.5h; pH=1 - 2;	96.6%
With tetrabutyl ammonium fluoride In dichloromethane at 20℃;	90%

: 1421704-60-0
3-((3S,8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pyridine

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 30℃; for 1h;	96.5%
Stage #1: 3-((3S,8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pyridine With tetrabutyl ammonium fluoride In tetrahydrofuran Stage #2: With water In tetrahydrofuran	89%
With tetrabutyl ammonium fluoride In tetrahydrofuran	89%

: C43H45NO

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 30℃; for 1h;	96.1%

: C29H39NO2

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 30℃; for 4h; pH=1 - 2;	94%

: C20H27F3O4S

: 89878-14-8
3-Diethylboranylpyridine

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 75℃; for 0.5h;	88.8%

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 89878-14-8
3-Diethylboranylpyridine

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; XPhos In 1,4-dioxane for 16h; Reflux;	75%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water at 70 - 75℃; for 22h; Solvent; Reagent/catalyst; Temperature;	74.1%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Suzuki Coupling; Reflux; Autoclave; Large scale;	72.1%

: 220565-63-9
pyridin-3-ylzinc(II) bromide

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 5h;	74.5%

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 21970-14-9
pyridin-3-ylmagnesium bromide

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 35℃; for 5h; Temperature;	72.31%

: 89878-14-8
3-Diethylboranylpyridine

: 106874-28-6
17-bromo-3β-hydroxy-5α-androstan-5,16-diene

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; tert-butyl alcohol for 3h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Suzuki Coupling; Inert atmosphere; Reflux; Large scale;	72%

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 1692-25-7
3-pyridylboronic acid

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 75 - 80℃; for 36h;	71.8%
With palladium on activated charcoal; sodium carbonate In dimethyl sulfoxide at 120℃; for 12h;

: 89878-14-8
3-Diethylboranylpyridine

: 17-iodoandrosta-5,16-dien-3β-ol 3-acetate

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Stage #1: 3-Diethylboranylpyridine; 17-iodoandrosta-5,16-dien-3β-ol 3-acetate With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 5h; Reflux; Large scale; Stage #2: With sodium hydroxide In methanol at 25 - 35℃; for 7h; Reagent/catalyst; Large scale;	67.8%
Stage #1: 3-Diethylboranylpyridine; 17-iodoandrosta-5,16-dien-3β-ol 3-acetate With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: With sodium carbonate In water at 65 - 70℃; for 1.25h;
Stage #1: 3-Diethylboranylpyridine; 17-iodoandrosta-5,16-dien-3β-ol 3-acetate With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: In tetrahydrofuran at 65 - 70℃; for 1.25h;	34 g

: 1003865-86-8
3-(dimethylboryl)pyridine

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In methanol; water at 65 - 70℃; for 28h;	65%

: 718628-27-4
C5H4INZn

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 4h;	52.5%

: C20H27F3O4S

: 197958-29-5
pyridin-2-ylboronic acid

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 2.5h; Time; Suzuki Coupling;	51.6%

: C26H38O3

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In acetonitrile Reflux;	50%

: 626-55-1
3-Bromopyridine

: 34988-34-6
dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Stage #1: dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; XPhos In 1,4-dioxane at 20℃; for 0.0833333h; Stage #2: 3-Bromopyridine With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 120℃; for 9h; Concentration; Temperature; Inert atmosphere;	43.1%
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; XPhos In 1,4-dioxane for 4h; Inert atmosphere; Reflux;
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; XPhos In 1,4-dioxane for 4h; Inert atmosphere; Reflux;
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; XPhos In 1,4-dioxane for 4h; Reflux;

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 81745-82-6
pyridin-3-ylzinc chloride

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 7h;	35.7%

: 53-43-0
dehydroepiandrosterone

3α-hydroxy-androsten-(5)-one-(17): 3α-hydroxy-androsten-(5)-one-(17)

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / NH2NH2H2O, aq, NH2NH2H2SO4 / ethanol / 120 h / Ambient temperature 2: 83 percent / I2, 1,1,3,3-tetramethylguanidine / tetrahydrofuran; diethyl ether / 1 h 3: 2 M aq. Na2CO3 / bis(triphenylphosphine)palladium(II) chloride / tetrahydrofuran / 96 h / 80 °C View Scheme

: 63015-10-1
dehydroepiandrosterone-17-hydrazone

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / I2, 1,1,3,3-tetramethylguanidine / tetrahydrofuran; diethyl ether / 1 h 2: 2 M aq. Na2CO3 / bis(triphenylphosphine)palladium(II) chloride / tetrahydrofuran / 96 h / 80 °C View Scheme
Multi-step reaction with 5 steps 1: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran / 1 h / Cooling with ice 2: 1H-imidazole / dichloromethane / 1 h / 20 °C 3: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - -65 °C 4: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 5 steps 1.1: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran 2.1: 1H-imidazole / dichloromethane / 1.17 h / 20 °C 3.1: triethyl borate / tetrahydrofuran / 0.17 h / -78 °C 3.2: 0.17 h / -65 °C 4.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran; toluene / Inert atmosphere; Reflux 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 853-23-6
prasterone acetate

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 12 h 2: 84 percent / bis(triphenylphosphine)palladium(II) chloride, aq. Na2CO3 / tetrahydrofuran / 1 h / 80 °C 3: 79 percent / aq. NaOH / methanol / 0.08 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux 3.1: potassium hydroxide; methanol / 1.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / dichloromethane / -78 - -20 °C 2: sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 1 h / 60 °C 3: potassium carbonate / methanol / 20 °C View Scheme

: 115375-60-5
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / bis(triphenylphosphine)palladium(II) chloride, aq. Na2CO3 / tetrahydrofuran / 1 h / 80 °C 2: 79 percent / aq. NaOH / methanol / 0.08 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux 2: potassium hydroxide; methanol / 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 1 h / 60 °C 2: potassium carbonate / methanol / 20 °C View Scheme

Et2: Et2

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 89878-14-8
3-Diethylboranylpyridine

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With sodium carbonate

...Expand

: 60-29-7
diethyl ether

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

: 89878-14-8
3-Diethylboranylpyridine

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran; bis(triphenylphosphine)palladium(II) dichloride

...Expand

: 53-43-0
dehydroepiandrosterone

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / Inert atmosphere; Reflux 2: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: water; tris-(dibenzylideneacetone)dipalladium(0); XPhos; lithium tert-butoxide / 1,4-dioxane / 5 h / Inert atmosphere; Reflux 4: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / Inert atmosphere; Reflux 2: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: water; tris-(dibenzylideneacetone)dipalladium(0); XPhos; lithium tert-butoxide / 1,4-dioxane / 6 h / 90 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 6 steps 1: hydrazinium sulfate; hydrazine hydrate / ethanol; water / 72 h / 20 °C 2: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran / 1 h / Cooling with ice 3: 1H-imidazole / dichloromethane / 1 h / 20 °C 4: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - -65 °C 5: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux 6: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 1426400-02-3
3-((tert-butyldimethylsilyl)oxy)-17-iodo-5,16-androstadiene

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - -65 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1.1: triethyl borate / tetrahydrofuran / 0.17 h / -78 °C 1.2: 0.17 h / -65 °C 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran; toluene / Inert atmosphere; Reflux 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 1426400-03-4
3-((tert-butyldimethylsilyl)oxy)-5,16-androstadien-17-boronic acid

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 34988-34-6
dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: water; tris-(dibenzylideneacetone)dipalladium(0); XPhos; lithium tert-butoxide / 1,4-dioxane / 5 h / Inert atmosphere; Reflux 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; lithium tert-butoxide / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 2.17 h / 20 °C / Inert atmosphere 2: caesium carbonate; dichloro bis(acetonitrile) palladium(II); 1,3-bis-(diphenylphosphino)propane / 1,4-dioxane / 110 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 5-dehydroepiandrosterone 2,4,6-trimethylbenzenesulfonyl hydrazone

: 154229-19-3
abiraterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: water; tris-(dibenzylideneacetone)dipalladium(0); XPhos; lithium tert-butoxide / 1,4-dioxane / 6 h / 90 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; XPhos / water; 1,4-dioxane / 6 h / 90 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran View Scheme

: 4530-20-5
BOC-glycine

: 154229-19-3
abiraterone

: tert-butoxycarbonylaminoacetic acid 10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	98%

: 154229-19-3
abiraterone

: 154229-21-7
17-(3-pyridine)-4,16-dieneandrost-3-one

Conditions

Conditions	Yield
With aluminum isopropoxide In toluene; butanone Inert atmosphere; Reflux;	97%
With aluminum isopropoxide In cyclohexanone; toluene for 2h; Dean-Stark; Reflux;	90%
With aluminum isopropoxide; butanone In toluene for 16h; Oppenauer Oxidation; Reflux; Dean-Stark;	85%

: 108-24-7
acetic anhydride

: 154229-19-3
abiraterone

: 154229-18-2
abiraterone acetate

Conditions

Conditions	Yield
With dmap In acetone at 20 - 65℃; for 1h;	95.3%
With pyridine; dmap; triethylamine at 0 - 20℃; for 5h;	95%
With pyridine In acetonitrile Reflux; Large scale;	91.6%

: 15026-17-2
succinic acid mono-tert-butyl ester

: 154229-19-3
abiraterone

: C32H43NO4

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h; Inert atmosphere;	95%

: 530-62-1
1,1'-carbonyldiimidazole

: 154229-19-3
abiraterone

: C28H33N3O2

Conditions

Conditions	Yield
Stage #1: abiraterone With triethylamine In dichloromethane for 0.166667h; Stage #2: 1,1'-carbonyldiimidazole With dmap In dichloromethane Reflux;	92%

: 79-04-9
chloroacetyl chloride

: 154229-19-3
abiraterone

: abiraterone chloroacetic acid ester

Conditions

Conditions	Yield
Stage #1: abiraterone With pyridine; calcium chloride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: chloroacetyl chloride In tetrahydrofuran at 0 - 20℃; for 10.5h; Solvent; Reagent/catalyst; Concentration; Temperature;	91.3%

: 75-36-5
acetyl chloride

: 154229-19-3
abiraterone

: 154229-18-2
abiraterone acetate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 4h;	85.1%
With 2-(Dimethylamino)pyridine; triethylamine In diethyl ether; ethanol; hexane; water	84%
With triethylamine In ethyl acetate at 5 - 20℃; for 2h;	83%

: [2-(tert-butoxycarbonyl-isopropylamino)acetylamino]acetic acid

: 154229-19-3
abiraterone

: [2-(tert-butoxycarbonylisopropylamino)acetylamino]acetic acid 10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	84%

: 154229-19-3
abiraterone

: 17β-(3-pyridyl)androst-5-en-3β-ol

Conditions

Conditions	Yield
With hydrazine hydrate; acetic acid In ethanol at 80℃; for 16h;	83%

: n-tetradecyloxy isopropenyl ether

: 154229-19-3
abiraterone

: C41H65NO2

Conditions

Conditions	Yield
With dichloro-acetic acid In dichloromethane at 20℃; Schlenk technique;	83%

: 16649-49-3
Acetic anhydride-d6

: 154229-19-3
abiraterone

: (3β)-17-(3-pyridyl)androst-5,16-dienyl d3-acetate

Conditions

Conditions	Yield
With dmap In acetone at 55 - 65℃; for 2h;	82.4%

: 1449222-32-5
[Ru(2,2’:6’,2’’-terpyridine)(6,6'-dimethyl-2,2'-dipyridyl)Cl]Cl

: 154229-19-3
abiraterone

: [Ru(2,2':6',2''-terpyridine)(6,6'-dimethyl-2,2'-biquinoline)(abiraterone)]Cl2

Conditions

Conditions	Yield
In ethanol; water at 80℃; for 20h; Inert atmosphere;	81.5%

: 7693-46-1
4-Nitrophenyl chloroformate

: 154229-19-3
abiraterone

: abiraterone 4-nitrobenzene carbonate

Conditions

Conditions	Yield
With dmap at 20℃;	80.6%
In tetrahydrofuran at 0℃; for 3h; Reflux;	69%

: 71985-80-3
1-methylpiperidine-4-carboxylic acid hydrochloride

: 154229-19-3
abiraterone

: [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridyl)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] 1-methylpiperidine-4-carboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	80%

: 13154-24-0
triisopropylsilyl chloride

: 154229-19-3
abiraterone

: 3-((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-((triisopropylsilyl)oxy)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pyridine

Conditions

Conditions	Yield
Stage #1: abiraterone With 1H-imidazole In dichloromethane at 0℃; for 0.166667h; Stage #2: triisopropylsilyl chloride In dichloromethane at 20℃; for 44h;	80%

: 154229-19-3
abiraterone

: 154229-33-1
17-(3-pyridyl)-3,6-dioxoandrosta-4,16-diene

Conditions

Conditions	Yield
With dipyridine chromium(VI) oxide In dichloromethane at 20℃; for 4h;	75%

: 4-((9Z,12Z)-octadeca-9,12-dien-1-yloxy)-4-oxobutanoic acid

: 154229-19-3
abiraterone

: (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl linoleylsuccinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 14h; Inert atmosphere; Cooling with ice;	60%

Abiraterone Specification

1. Introduction of Abiraterone
Abiraterone is one kind of white powder. Abiraterone IUPAC name is called (3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol. Abiraterone belongs to the product categories of API; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. Lipophilic compound is a Lipophilic compound and can not soluble in water.

2. Properties of Abiraterone
Physical properties about Abiraterone are:
(1)ACD/LogP: 5.661; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.45; (4)ACD/LogD (pH 7.4): 5.66; (5)ACD/BCF (pH 5.5): 7195.82; (6)ACD/BCF (pH 7.4): 11721.29; (7)ACD/KOC (pH 5.5): 17428.90; (8)ACD/KOC (pH 7.4): 28390.01; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 33.12 Å²; (13)Index of Refraction: 1.606; (14)Molar Refractivity: 105.19 cm³; (15)Molar Volume: 305.16 cm³; (16)Surface Tension: 50.07 dyne/cm; (17)Density: 1.145 g/cm³; (18)Flash Point: 256.294 °C; (19)Enthalpy of Vaporization: 80.951 kJ/mol; (20)Boiling Point: 500.17 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

3. Structure Descriptors of Abiraterone
(1) SMILES: O[C@@H]2C/C1=C/C[C@@H]4[C@@H]([C@@]1(C)CC2)CC[C@@]3(C(=C/C[C@H]34)\c5cccnc5)C
(2) InChI: InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
(3) InChIKey: GZOSMCIZMLWJML-VJLLXTKPSA-N

4. Uses of Abiraterone
Abiraterone is a drug used in castration-resistant prostate cancer. It is formulated as the prodrug abiraterone acetate. Abiraterone can be used as a prostate cancer drug treatment. Abiraterone is a inhibitor of CYP17. It can be used to treat CRPC.

5. History of Abiraterone
This drug was discovered by Gerry Potter in 1990 at the Cancer Research UK Centre for Cancer Therapeutics within the Institute of Cancer Research in London. Rights for commercialisation of the drug were assigned to BTG plc, a UK company that manages commercialisation activity in pharmaceuticals. BTG then licenced the product to Cougar Biotechnology which began development of the commercial product. In 2009, Cougar was acquired by Johnson & Johnson which developed and sells the commercial product, and is conducting ongoing clinical trials to expand its clinical uses.

Product Name

Abiraterone

Synthetic route

Abiraterone Specification

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