641-77-0

Usage

Uses

Used in Pharmaceutical Industry:
11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE is used as a metabolite of Fluticasone propionate (F599500) for its potential therapeutic applications. Fluticasone propionate is a corticosteroid used in the treatment of various inflammatory conditions, such as asthma, allergies, and skin disorders. As a metabolite, 11BETA,17ALPHA-DIHYDROXY-4-PREGNENE-3,20-DIONE may contribute to the overall efficacy and safety profile of Fluticasone propionate-based medications.
Additionally, as a metabolite, it may be used in research and development for understanding the metabolic pathways and pharmacokinetics of Fluticasone propionate, which can help in optimizing its therapeutic use and minimizing potential side effects.

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

• 68-96-2 17-hydroxyprogesterone 
• 103795-86-4 4β-bromo-11β,17-dihydroxy-5β-pregnane-3,20-dione 
• 33767-06-5 11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione 
• 6677-96-9 11β,7α-dihydroxy-21-<(methylsulfonyl)oxy>pregn-4-ene-3,20-dione 
• 114585-39-6 3,3-ethanediyldioxy-4β-chloro-11β,17-dihydroxy-5β-pregnan-20-one 
• 63644-48-4 Cortisol 21-tosylate 
• 50-23-7 HYDROCORTISONE 
• 603-96-3 3α,11α,17-trihydroxy-5β-pregnan-20-one 
• 74263-44-8 11β,17-dihydroxy-5β-pregnane-3,20-dione 
• 641-78-1 3α,17-dihydroxy-5β-pregnane-11,20-dione 
• 124226-80-8 3,3;20,20-bis-ethanediyldioxy-4β-chloro-17-hydroxy-5β-pregnan-11-one 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

Dehalogenation methodof 9-halogenated steroid compound and application

The invention provides a dehalogenation method of a 9-halogenated steroid compound and application, and relates to the technical field of chemical synthesis. The dehalogenation method of the 9-halogenated steroid compound comprises the following steps: reacting a compound I with a hydrogen donor and an azo radical initiator to obtain a 9-dehalogenated product compound II of the 9-halogenated steroid compound. According to the dehalogenation method of the 9-halogenated steroid compound, a hydrogen donor adopts one or a combination of more of hypophosphorous acid and hypophosphite, formic acid and formate, organic silicon hydride, hydrazine compounds or cyclohexene, and an initiator adopts an azo free radical initiator. Reagents such as chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride which are high in toxicity and cause serious pollution to the environment are not used in the reaction, the method is green and environmentally friendly, the synthesis process is simple, convenient and easy to implement, and the production applicability is improved.

Methylprednisolone intermediate debrominated product and preparation method thereof

The invention discloses a methylprednisolone intermediate debrominated product and a preparation method thereof. According to the preparation method, a compound shown as a formula I is used as a raw material, and a dechlorination reaction, a bromination reaction, a debromination reaction and an oxidation reaction are sequentially performed to prepare a compound (debrominated substance) shown as aformula V. The preparation method has the advantages of short synthetic route, high yield, low cost and easily available raw materials, is suitable for industrial production, and has very high industrial value.

Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups

The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron-withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

REDUCTIVE DEHALOGENATION OF 21-IODO DERIVATIVES OF CORTICOSTEROIDS

In the reactions of 21-iodo derivatives of corticosteroids with hydrogen sulfide and thiol-containing reagents in a medium of dipolar aprotic and amide protogenic solvents at room temperature reductive-deiodination reactions occur with the formation of 21-deoxycorticosteroids in quantitative yield.Reactions of solutions of 21-iodomethyl ketones, heated to 80 deg C, with hydrogen sulfide and thiol-containing reagents give not only reduction products, but also products of nucleophilic substitution at C21 in yields of 20-30percent.

Process for preparing 3-enol ethers of 11β-hydroxy-Δ4 -pregnene-3-ones and derivatives thereof

3-enol ethers of 11β-hydroxy-Δ4 -pregnene-3-ones are prepared by reacting triethylorthoacetate with an 11β-hydroxy-Δ4 -pregnene-3-one in a solvent which is at least 40% by weight or more ethanol and 60% by weight or less of a compatible oxygenated hydrocarbon liquid in the presence of an acid catalyst. This reaction forms a basis of a process for forming 6-halo-derivatives, particularly 6-chloro-Δ1,4,6 -pregnatrien -11β,17α,21-triol-3,20-dione.