1882-82-2

Basic information

• Product Name: 21-DEOXYCORTISONE
• Synonyms: 17-Hydroxypregn-4-ene-3,11,20-trione;21-deoxycortisonecrystalline;4-PREGNEN-17-OL-3,11,20-TRIONE;4-PREGNEN-17-ALPHA-OL-3,11,20-TRIONE;17A-HYDROXY-4-PREGNEN-3,11,20-TRIONE;17-ALPHA-HYDROXY-4-PREGNENE-3,11,20-TRIONE;21-DEOXYCORTISONE;21-DESOXYCORTISONE
• CAS NO: 1882-82-2
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44
• EINECS: 217-541-5
• Product Categories: Steroids;Steroids & Hormones - 13C & 2H;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 1882-82-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 236-239 °C
• Boiling Point: 524.571 °C at 760 mmHg
• Flash Point: 285.129 °C
• Appearance: /
• Density: 1.21
• Vapor Pressure: 3.39E-13mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 12.76±0.60(Predicted)
• CAS DataBase Reference: 21-DEOXYCORTISONE(CAS DataBase Reference)
• NIST Chemistry Reference: 21-DEOXYCORTISONE(1882-82-2)
• EPA Substance Registry System: 21-DEOXYCORTISONE(1882-82-2)

Safety Data

• Hazardous Substances Data: 1882-82-2(Hazardous Substances Data)

Usage

Uses

A Cortisone derivative, a glucocorticoid.

InChI:InChI=1/C21H28O4/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/h10,15-16,18,25H,4-9,11H2,1-3H3/t15-,16-,18+,19-,20-,21-/m0/s1

Synthetic route

21-iodocortisone (5758-63-4) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With mercaptoacetic acid In N,N-dimethyl-formamide for 0.25h; Ambient temperature;	99.7%

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%

2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl methanesulfonate (5783-48-2) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With sodium iodide; zinc In 1,2-dimethoxyethane; water for 5h; Heating;	89%

17,21-dihydroxy-pregn-4-ene-3,11,20-trione (53-06-5, 10007-36-0, 15779-07-4, 35446-72-1, 104713-00-0) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride Erwaermen des Reaktionsprodukts mit NaI und Essigsaeure;
With pyridine; methanesulfonyl chloride Erwaermen des Reaktionsprodukts mit NaI und Essigsaeure;

11α,17α-dihydroxypregn-4-ene-3,20-dione (603-98-5) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With chromium(VI) oxide; acetic acid
With pyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; O-phenyl phosphorodichloridate In dimethyl sulfoxide; 1,2-dichloro-ethane at 0℃; for 3.5h;	9.7 g
With N-chloro-succinimide In chloroform; dimethyl sulfoxide at -30℃; Temperature; Reagent/catalyst;	9.07 g

3β,11α,17-trihydroxy-pregn-5-en-20-one (17276-51-6) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid; acetone Isomerisierung des Reaktionsprodukts mit HCl und Essigsaeure;

4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione (114160-28-0) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With semicarbazide hydrochloride; sodium acetate Behandeln anschliessend mit Brenztraubensaeure;

4β-bromo-17-hydroxy-5β-pregnane-3,11,20-trione (111584-17-9) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With pyridine

17-hydroxy-5β-pregnane-3,11,20-trione (10455-93-3) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With bromine Erhitzen des Reaktionsprodukts mit Pyridin;
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: pyridine View Scheme

16β-iodo-17-hydroxy-pregn-4-ene-3,11,20-trione → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With ethanol; nickel

17-hydroxyprogesterone (68-96-2) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: mit Hilfe von Rhizopus nigricans 2: CrO3; acetic acid View Scheme

3α,17-dihydroxy-5β-pregnane-11,20-dione (641-78-1) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3; water containing acetic acid 2: bromine / Erhitzen des Reaktionsprodukts mit Pyridin View Scheme
Multi-step reaction with 3 steps 1: tert-butyl alcohol; N-bromo-acetamide 2: acetic acid; bromine 3: pyridine View Scheme
Multi-step reaction with 2 steps 1: tert-butyl hypochlorite; water; tert-butyl alcohol; HCl 2: aqueous semicarbazide hydrochloride; sodium acetate / Behandeln anschliessend mit Brenztraubensaeure View Scheme

(17Ξ)-3α,11,20-triacetoxy-5β-pregna-9(11),17(20)-diene (115484-65-6) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: peroxybenzoic acid; benzene / Behandeln des Reaktionsprodukts mit wss.-aethanol.NaOH 2: tert-butyl alcohol; N-bromo-acetamide 3: acetic acid; bromine 4: pyridine View Scheme

3α,11α,17-trihydroxy-5β-pregnan-20-one (603-96-3) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 3 steps 2: CrO3; pyridine 3: aqueous semicarbazide hydrochloride; sodium acetate / Behandeln anschliessend mit Brenztraubensaeure View Scheme

4β-chloro-11α,17-dihydroxy-5β-pregnane-3,20-dione → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3; pyridine 2: aqueous semicarbazide hydrochloride; sodium acetate / Behandeln anschliessend mit Brenztraubensaeure View Scheme

20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one (116105-53-4) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiAlH4 / folgenden mit wss.HCl 3: CrO3; pyridine 4: aqueous semicarbazide hydrochloride; sodium acetate / Behandeln anschliessend mit Brenztraubensaeure View Scheme

3β,11α-diacetoxy-17-hydroxy-pregn-5-en-20-one (115485-81-9) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol.KOH 2: CrO3; H2SO4; acetone / Isomerisierung des Reaktionsprodukts mit HCl und Essigsaeure View Scheme

3β,11α-diacetoxy-16β-bromo-17-hydroxy-pregn-5-en-20-one (115963-58-1) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium/charcoal / Hydrogenation 2: methanol.KOH 3: CrO3; H2SO4; acetone / Isomerisierung des Reaktionsprodukts mit HCl und Essigsaeure View Scheme

21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione (75868-48-3) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrafluoroboric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / butanone; water / 3.5 h / 0 - 5 °C / Inert atmosphere 2: Jones reagent / tetrahydrofuran / 2 h / 0 - 5 °C 3: acetic acid; zinc / tetrahydrofuran / 11 h / 20 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 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 4: Jones reagent / butanone / 2 h / 0 - 9 °C View Scheme

C21H26BrClO4 → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
With acetic acid; zinc In tetrahydrofuran at 20 - 55℃; for 11h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;	80.6 g

pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl (34184-82-2) → 17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2)

Conditions	Yield
Multi-step reaction with 3 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 3: Jones reagent / butanone / 2 h / 0 - 9 °C View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) + trimethyl orthoformate (149-73-5) → 17α-hydroxy-3-methoxypregna-3,5-diene-11,20-dione (82937-74-4)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane for 1.25h; Ambient temperature;	76.5%

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 21-hydroxy-1,4-pregnadiene-3,11,20-trione (67067-81-6)

Conditions	Yield
mit Hilfe von Corynebacterium simplex;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 17-hydroxy-5α-pregnane-3,11,20-trione (1923-68-8)

Conditions	Yield
With Pd-BaSO4; ethyl acetate Hydrogenation;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) + ethylene glycol (107-21-1) → 3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one (74332-34-6)

Conditions	Yield
With toluene-4-sulfonic acid; benzene
With trimethyloxosulfonium bromide; orthoformic acid triethyl ester for 5h;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → (8S,9S,10R,13S,14S,17R)-17-Hydroxy-17-(1-hydroxy-ethyl)-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,11-dione (151283-62-4)

Conditions	Yield
With 20β-hydroxysteroid dehydrogenase at 25℃; Rate constant; pH 6.4;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 6β,17α-dihydroxy-5β-pregnane-3,11,20-trione (93064-67-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 76.5 percent / toluene-p-sulphonic acid / dioxane / 1.25 h / Ambient temperature 2: 45.6 percent / O2 / ethanol / 5 h / Irradiation 3: 54 percent / H2 / Pd-CaCO3 / pyridine View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 6β,17α-dihydroxy-pregn-4-ene-3,11,20-trione (93064-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76.5 percent / toluene-p-sulphonic acid / dioxane / 1.25 h / Ambient temperature 2: 45.6 percent / O2 / ethanol / 5 h / Irradiation View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 3α,6β,17,20α-tetrahydroxy-5β-pregnan-11-one 6-hemisuccinate (93064-69-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 76.5 percent / toluene-p-sulphonic acid / dioxane / 1.25 h / Ambient temperature 2: 45.6 percent / O2 / ethanol / 5 h / Irradiation 3: 54 percent / H2 / Pd-CaCO3 / pyridine 4: 34.3 percent / pyridine / 5 h / Heating 5: 23 percent / cerous chloride, sodium borohydrode / methanol / 5 h / Ambient temperature View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 6β,17α-dihydroxy-5β-pregnane-3,11,20-trione 6-hemisuccinate (93064-68-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 76.5 percent / toluene-p-sulphonic acid / dioxane / 1.25 h / Ambient temperature 2: 45.6 percent / O2 / ethanol / 5 h / Irradiation 3: 54 percent / H2 / Pd-CaCO3 / pyridine 4: 34.3 percent / pyridine / 5 h / Heating View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → pregnane-4,9(11),16(17)-triene-3,20-dione (21590-20-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene; toluene-4-sulfonic acid 2: sodium borate; ethanol 3: thionyl chloride; pyridine 4: aqueous acetic acid View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 16α,17α-dihydroxy-17β-methyl-D-homo-androsta-4,9(11)-diene-3,17a-dione (114035-27-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: benzene; toluene-4-sulfonic acid 2: sodium borate; ethanol 3: thionyl chloride; pyridine 4: aqueous acetic acid 5: OsO4 6: Al2O3 View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 16α,17-dihydroxy-pregna-4,9(11)-diene-3,20-dione (2135-08-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: benzene; toluene-4-sulfonic acid 2: sodium borate; ethanol 3: thionyl chloride; pyridine 4: aqueous acetic acid 5: OsO4 View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 11-oxomedroxyprogesterone (82332-00-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: benzene; toluene-4-sulfonic acid 2: chloroform; diethyl ether 3: benzene 4: aqueous methanol.H2SO4 5: methanol.KOH View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / dichloromethane; water 2: N-methylaniline; hydrogenchloride / tetrahydrofuran 3: hydrogenchloride; palladium on activated charcoal / ethanol; cyclohexene View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 5,17-dihydroxy-6β-methyl-5α-pregnane-3,11,20-trione (111767-44-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene; toluene-4-sulfonic acid 2: chloroform; diethyl ether 3: benzene 4: aqueous methanol.H2SO4 View Scheme

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 21-acetoxy-17-hydroxy-6α-methyl-pregn-4-ene-3,11,20-trione (3751-03-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: benzene; toluene-4-sulfonic acid 2: chloroform; diethyl ether 3: benzene 4: aqueous methanol.H2SO4 5: methanol.KOH 6: iodine; CaO; methanol / Reagens 4: THF; beim anschliessenden Erwaermen mit Kaliumacetat in Aceton View Scheme

Upstream product

• 641-77-0 21-deoxycortisol 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 75868-48-3 21-chloro-17-hydroxy-pregna-4,9⁽¹¹⁾-diene-3,20-dione 
• 115963-58-1 3β,11α-diacetoxy-16β-bromo-17-hydroxy-pregn-5-en-20-one 
• 115485-81-9 3β,11α-diacetoxy-17-hydroxy-pregn-5-en-20-one 
• 116105-53-4 20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one 
• 603-96-3 3α,11α,17-trihydroxy-5β-pregnan-20-one 
• 115484-65-6 (17Ξ)-3α,11,20-triacetoxy-5β-pregna-9(11),17(20)-diene 
• 641-78-1 3α,17-dihydroxy-5β-pregnane-11,20-dione 
• 68-96-2 17-hydroxyprogesterone 
• 5783-48-2 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl methanesulfonate 
• 5758-63-4 21-iodocortisone 
• 10455-93-3 17-hydroxy-5β-pregnane-3,11,20-trione 
• 111584-17-9 4β-bromo-17-hydroxy-5β-pregnane-3,11,20-trione 

Downstream Products

• 6870-94-6 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 
• 53-36-1 methylprednisolone acetate 
• 83-43-2 Methylprednisolone 
• 1625-39-4 11β,17α,21-trihydroxy-6α-methylpregna-4-ene-3,20-dione 
• 7055-53-0 11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione 
• 1923-68-8 17-hydroxy-5α-pregnane-3,11,20-trione 
• 67067-81-6 21-hydroxy-1,4-pregnadiene-3,11,20-trione 

Relevant articles and documents

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Pregnane-4-ene-17alpha-ol-3,11,20-trione preparation method

The invention relates to a pregnane-4-ene-17alpha-ol-3,11,20-trione preparation method, which comprises: using a compound I as a raw material, adding a bromination reagent, and carrying out a 9,11-site bromo-hydroxyl reaction to obtain a compound II; mixing the compound II and an oxidizing agent, and carrying out an oxidation reaction, wherein the hydroxyl at the 11th position in the compound II is oxidized into a ketone group to obtain a compound III; and carrying out a reduction dehalogenation reaction on the compound III to obtain pregnane-4-ene-17alpha-ol-3,11,20-trione, wherein the structural formulas of the compound I, the compound II and the compound III are represented by the specification. According to the invention, the preparation method is short in synthetic route, high in product yield, low in cost and suitable for industrial production of pregnane-4-ene-17alpha-ol-3,11,20-trione.

Multi-hydroxy pregnane 11 α hydroxy selective oxidation method

The invention provides a selective oxidation method for selective oxidation method for polyhydroxy-pregna-11alpha-hydroxy. According to the invention, pregna-4-ene-3,20-diketone-11alpha,17alpha-dihydroxy is used as a substrate and reacts with dimethyl sulfoxide and an activator in liquid chloroalkane, and alkali is added after completion of the reaction so as to adjust a pH value to 8.5 to 10, thereby obtaining pregna-4-ene-3,11,20-triketone-17alpha-hydroxy.