641-77-0

Basic information

• Product Name: 11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE
• Synonyms: 21-deoxycortisol;21 DEOXYCORTISOL 21-DESOXYCORTISOL;21-DESOXYCORTISOL;11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE;11BETA,17ALPHA-DIHYDROXY-PROGESTERONE;4-PREGNENE-11BETA,17ALPHA-DIOL-3,20-DIONE;4-PREGNEN-11BETA,17ALPHA-DIOL-3,20-DIONE;4-PREGNEN-11-BETA, 17-DIOL-3,20-DIONE
• CAS NO: 641-77-0
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.46
• EINECS: 211-375-7
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 641-77-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 225-228 °C
• Boiling Point: 523.9°C at 760 mmHg
• Flash Point: 9℃
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 3.64E-13mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 12.86±0.70(Predicted)
• CAS DataBase Reference: 11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE(641-77-0)
• EPA Substance Registry System: 11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE(641-77-0)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 641-77-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 641-77-0 differently. You can refer to the following data:
1. 21-Deoxy Cortisol (Hydrocortisone EP Impurity L) is a metabolite of Fluticasone propionate (F599500).
2. A metabolite of Fluticasone propionate (F599500).

InChI:InChI=1/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3

Synthetic route

11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione (33767-06-5) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With 3-mercaptopropionic acid In N,N-dimethyl acetamide for 0.166667h; Ambient temperature;	98.9%
With pyridine; iodine; triphenylphosphine In toluene for 6h; Inert atmosphere; Reflux;	20%
With acetic acid; zinc

11β,17α-dihydroxy-17-pregn-4-en-20-yn-3-one (137174-13-1) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With mercury(II) sulfate In tetrahydrofuran; methanol at 20℃; for 1.5h;	82%

HYDROCORTISONE (50-23-7) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With pyridine; iodine; triphenylphosphine In toluene for 6h; Inert atmosphere; Reflux; chemoselective reaction;	79%
Multi-step reaction with 2 steps 2: NaI; acetic acid View Scheme
Multi-step reaction with 2 steps 1: Py 2: NaI, Zn / 1,2-dimethoxy-ethane; H2O / Heating View Scheme

11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione (33767-06-5) → 21-deoxycortisol (641-77-0) + 11β,17α-dihydroxy-21-mercapto-4-pregnene-3,20-dione (61951-99-3)

Conditions	Yield
With hydrogen sulfide In N,N-dimethyl-formamide at 80℃; for 0.25h;	A 61% B 29.5%

17-hydroxyprogesterone (68-96-2) → 21-deoxycortisol (641-77-0)

Conditions	Yield
mit Hilfe von Curvularia lunata;

4β-bromo-11β,17-dihydroxy-5β-pregnane-3,20-dione (103795-86-4) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With hydrazine carboxamide nachfolgende Umsetzung mit Brenztraubensaeure;

11β,7α-dihydroxy-21-<(methylsulfonyl)oxy>pregn-4-ene-3,20-dione (6677-96-9) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With acetic acid; sodium iodide
With sodium iodide; zinc In 1,2-dimethoxyethane; water Heating;

3,3-ethanediyldioxy-4β-chloro-11β,17-dihydroxy-5β-pregnan-20-one (114585-39-6) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With sulfuric acid nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure;

Cortisol 21-tosylate (63644-48-4) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With hydrogen sulfide; sodium iodide 1.) EtOH, DMF, reflux, 10 min, 2.) EtOH, DMF; Yield given. Multistep reaction;

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione (382-44-5) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / ethylenediamine / toluene / 2 h 2: 32 percent / ethylenediamine / diethyl ether / 2 h 3: 82 percent / HgSO4 / methanol; tetrahydrofuran / 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 6 mg / ethylenediamine / toluene / 2 h 2: 82 percent / HgSO4 / methanol; tetrahydrofuran / 1.5 h / 20 °C View Scheme

11β-hydroxy-17α-ethynyl-17β-hydroxy-4-androsten-3-one (69065-06-1) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 32 percent / ethylenediamine / diethyl ether / 2 h 2: 82 percent / HgSO4 / methanol; tetrahydrofuran / 1.5 h / 20 °C View Scheme

9α-bromo-11β-hydroxy-17α-ethynyl-17β-hydroxy-4-androsten-3-one (139562-74-6) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / α',α'-isobutyronitrile, HBu3Sn / tetrahydrofuran / 3.5 h / Heating 2: 32 percent / ethylenediamine / diethyl ether / 2 h 3: 82 percent / HgSO4 / methanol; tetrahydrofuran / 1.5 h / 20 °C View Scheme

4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione (114160-28-0) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene; toluene-4-sulfonic acid 2: lithium alanate; diethyl ether; benzene 3: acetone; aqueous sulfuric acid 4: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

3α,11α,17-trihydroxy-5β-pregnan-20-one (603-96-3) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 6 steps 2: CrO3; pyridine 3: benzene; toluene-4-sulfonic acid 4: lithium alanate; diethyl ether; benzene 5: acetone; aqueous sulfuric acid 6: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

11β,17-dihydroxy-5β-pregnane-3,20-dione (74263-44-8) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: DMF; bromine 2: semicarbazide / nachfolgende Umsetzung mit Brenztraubensaeure View Scheme

3α,17-dihydroxy-5β-pregnane-11,20-dione (641-78-1) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: tert-butyl hypochlorite; water; tert-butyl alcohol; HCl 2: benzene; toluene-4-sulfonic acid 3: lithium alanate; diethyl ether; benzene 4: acetone; aqueous sulfuric acid 5: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

4β-chloro-11α,17-dihydroxy-5β-pregnane-3,20-dione → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: CrO3; pyridine 2: benzene; toluene-4-sulfonic acid 3: lithium alanate; diethyl ether; benzene 4: acetone; aqueous sulfuric acid 5: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

3,3;20,20-bis-ethanediyldioxy-4β-chloro-5β-pregnane-11β,17-diol (124115-91-9) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; aqueous sulfuric acid 2: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

3,3;20,20-bis-ethanediyldioxy-4β-chloro-17-hydroxy-5β-pregnan-11-one (124226-80-8) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium alanate; diethyl ether; benzene 2: acetone; aqueous sulfuric acid 3: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one (116105-53-4) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 7 steps 1: LiAlH4 / folgenden mit wss.HCl 3: CrO3; pyridine 4: benzene; toluene-4-sulfonic acid 5: lithium alanate; diethyl ether; benzene 6: acetone; aqueous sulfuric acid 7: aqueous H2SO4 / nachfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure View Scheme

21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione (75868-48-3) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc; acetic acid / butanone / 50 - 55 °C 2: water; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; tetrafluoroboric acid / acetone / 3 h / 0 - 5 °C / Inert atmosphere 3: chromium chloride; mercaptoacetic acid; zinc / dimethyl sulfoxide / 2 h / 0 - 5 °C / Inert atmosphere View Scheme

pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl (34184-82-2) → 21-deoxycortisol (641-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; tetrafluoroboric acid / acetone / 3 h / 0 - 5 °C / Inert atmosphere 2: chromium chloride; mercaptoacetic acid; zinc / dimethyl sulfoxide / 2 h / 0 - 5 °C / Inert atmosphere View Scheme

9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione (102445-69-2) → 21-deoxycortisol (641-77-0)

Conditions	Yield
With chromium chloride; mercaptoacetic acid; zinc In dimethyl sulfoxide at 0 - 5℃; for 2h; Solvent; Inert atmosphere;

21-deoxycortisol (641-77-0) + acetic anhydride (108-24-7) → 11β-acetoxy-17α-hydroxy-4-pregnene-3,20-dione (806-46-2)

Conditions	Yield
With pyridine; dmap at 20℃; for 6h;	100%
With pyridine

21-deoxycortisol (641-77-0) → 11β-acetoxy-17α-hydroxy-4-pregnene-3,20-dione (806-46-2)

Conditions	Yield
With pyridine; dmap; acetic anhydride In hexane; chloroform	100%

21-deoxycortisol (641-77-0) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With Jones reagent In butanone at 0 - 9℃; for 2h; Solvent;	98.2%

21-deoxycortisol (641-77-0) → pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl (34184-82-2)

Conditions	Yield
With pyridine; iodine; triphenylphosphine In toluene Inert atmosphere; Reflux; chemoselective reaction;	12%

21-deoxycortisol (641-77-0) → (8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-11,17-dihydroxy-10,13-dimethyl-tetradecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthren-3-one

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol at 0℃; for 3h;

21-deoxycortisol (641-77-0) → 9α-Fluoro-17α-hydroxy-6-methyl-4-pregnene-3,20-dione (171611-81-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C 6: aq. NaOH / methanol / 2 h / 20 °C 7: 23.3 percent / hydrogen fluoride; pyridine / 60 h / -15 °C View Scheme

21-deoxycortisol (641-77-0) → 6-methyl-4-pregnene-11β,17α-diol-3,20-dione (111819-45-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C 6: aq. NaOH / methanol / 2 h / 20 °C View Scheme

21-deoxycortisol (641-77-0) → (8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-5,11,17-trihydroxy-6,10,13-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one (171865-12-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C View Scheme

21-deoxycortisol (641-77-0) → C26H39FO5 (171611-82-8)

Conditions

Yield

Multi-step reaction with 8 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C 6: aq. NaOH / methanol / 2 h / 20 °C 7: 23.3 percent / hydrogen fluoride; pyridine / 60 h / -15 °C 8: p-TsOH / benzene / 3 h / Heating View Scheme

21-deoxycortisol (641-77-0) → C26H42O7 (171754-63-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating View Scheme

21-deoxycortisol (641-77-0) → C27H40O8 (171611-80-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C View Scheme

21-deoxycortisol (641-77-0) → 17α-acetoxy-9α-fluoro-6α-methylprogesterone

Conditions

Yield

Multi-step reaction with 10 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C 6: aq. NaOH / methanol / 2 h / 20 °C 7: 23.3 percent / hydrogen fluoride; pyridine / 60 h / -15 °C 8: p-TsOH / benzene / 3 h / Heating 9: 23 mg / aq. KHSO4 / acetone / 2 h / 70 °C 10: 36 percent / p-TsOH / CH2Cl2 / 5 h / -10 °C View Scheme

21-deoxycortisol (641-77-0) → C27H40O7 (187244-71-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine 2: p-TSA View Scheme

21-deoxycortisol (641-77-0) → 9α-fluoro-17α-hydroxy-6α-methyl-4-pregnene-3,20-dione (171754-64-6)

Conditions

Yield

Multi-step reaction with 9 steps 1: 100 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C 2: p-TsOH / benzene / 7 h / Heating 3: m-chloroperbenzoic acid / CHCl3 / 12 h / 20 °C 4: tetrahydrofuran / 18 h / Heating 5: aq. KHSO4 / acetone / 2 h / 70 °C 6: aq. NaOH / methanol / 2 h / 20 °C 7: 23.3 percent / hydrogen fluoride; pyridine / 60 h / -15 °C 8: p-TsOH / benzene / 3 h / Heating 9: 23 mg / aq. KHSO4 / acetone / 2 h / 70 °C View Scheme

21-deoxycortisol (641-77-0) → 4-(carboxymethylthio)-21-deoxycortisol (81983-33-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30percent H2O2, 10percent NaOH / methanol / 3 h / 0 °C 2: 25percent KOH / ethanol; dioxane / 2 h / Ambient temperature View Scheme

21-deoxycortisol (641-77-0) → 4-(2-carboxyethylthio)-21-deoxycortisol (81983-34-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30percent H2O2, 10percent NaOH / methanol / 3 h / 0 °C 2: 25percent KOH / ethanol; dioxane / 2 h / Ambient temperature View Scheme

21-deoxycortisol (641-77-0) → ((8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-ylsulfanyl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (81983-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 30percent H2O2, 10percent NaOH / methanol / 3 h / 0 °C 2: 25percent KOH / ethanol; dioxane / 2 h / Ambient temperature 3: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / dioxane; H2O / 2 h / Ambient temperature View Scheme

21-deoxycortisol (641-77-0) → 3-((8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-ylsulfanyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (81983-50-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 30percent H2O2, 10percent NaOH / methanol / 3 h / 0 °C 2: 25percent KOH / ethanol; dioxane / 2 h / Ambient temperature 3: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / dioxane; H2O / 2 h / Ambient temperature View Scheme

Upstream product

• 114585-39-6 3,3-ethanediyldioxy-4β-chloro-11β,17-dihydroxy-5β-pregnan-20-one 
• 33767-06-5 11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione 
• 63644-48-4 Cortisol 21-tosylate 
• 75868-48-3 21-chloro-17-hydroxy-pregna-4,9⁽¹¹⁾-diene-3,20-dione 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 102445-69-2 9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 116105-53-4 20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one 
• 124226-80-8 3,3;20,20-bis-ethanediyldioxy-4β-chloro-17-hydroxy-5β-pregnan-11-one 
• 124115-91-9 3,3;20,20-bis-ethanediyldioxy-4β-chloro-5β-pregnane-11β,17-diol 
• 641-78-1 3α,17-dihydroxy-5β-pregnane-11,20-dione 
• 74263-44-8 11β,17-dihydroxy-5β-pregnane-3,20-dione 
• 603-96-3 3α,11α,17-trihydroxy-5β-pregnan-20-one 
• 114160-28-0 4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione 
• 50-23-7 HYDROCORTISONE 

Downstream Products

• 1882-82-2 17-hydroxy-pregn-4-ene-3,11,20-trione 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 171611-77-1 17α-acetoxy-9α-fluoro-6α-methylprogesterone 

Relevant articles and documents

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