981-34-0

Basic information

• Product Name: 9beta,11beta-Epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione
• Synonyms: 16-BETA METHYL EPOXIDE;9beta,11beta-epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione;DB11;(9β)-9,11β-Epoxy-16β-methyl-17,21-dihydroxypregna-1,4-diene-3,20-dione;9β,11β-Epoxy-17,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione;Einecs 213-563-4;Betamethasone 9,11-Epoxide;9beta,11beta-Epoxy-1
• CAS NO: 981-34-0
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 370.44
• EINECS: 213-563-4
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 981-34-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 210-220 ºC
• Boiling Point: 564.9 °C at 760 mmHg
• Flash Point: 198.1 °C
• Appearance: off-white solid
• Density: 1.32 g/cm³
• Vapor Pressure: 4.09E-15mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: Refrigerator
• PKA: 12.56±0.70(Predicted)
• CAS DataBase Reference: 9beta,11beta-Epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 9beta,11beta-Epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione(981-34-0)
• EPA Substance Registry System: 9beta,11beta-Epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione(981-34-0)

Safety Data

• Hazardous Substances Data: 981-34-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 981-34-0 differently. You can refer to the following data:
1. Metabolite of Beclometasone (131000)
2. A metabolite of Mometasone furoate. Low solubility in most solvent.

InChI:InChI=1/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)22(15)18(27-22)10-20(16,3)21(12,26)17(25)11-23/h6-7,9,12,15-16,18,23,26H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,18-,19-,20-,21-,22+/m0/s1

Synthetic route

21-acetoxy-17α-hydroxy-9β,11β-epoxy-16β-methylpregna-4-ene-3,20-dione → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
With D-Glucose In aq. phosphate buffer for 76h; Microbiological reaction;	83%

C25H33BrO7 → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
In dichloromethane; water at 25 - 30℃; for 1h; Inert atmosphere;	75%
With sodium hydroxide In methanol; dichloromethane at 0 - 5℃;

Carbonic acid 2-((8S,9S,10R,11R,13S,14S,16S,17R)-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester ethyl ester → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus pentachloride / tetrahydrofuran / 1 h / -85 °C 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water / 0.25 h / 10 - 20 °C 3: sodium hydroxide / dichloromethane; water; methanol / 3 h / -5 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: phosphorus pentachloride / tetrahydrofuran / 1 h / -85 °C 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 3: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: phosphorus pentachloride; pyridine / dichloromethane / 0.75 h / 20 °C 2: dimethyl sulfoxide / 3 h / 90 °C 3: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water / 0.25 h / 10 - 20 °C 4: sodium hydroxide / dichloromethane; water; methanol / 3 h / -5 - 0 °C / Inert atmosphere View Scheme

C26H36O9S → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid / 115 °C 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water / 0.25 h / 10 - 20 °C 3: sodium hydroxide / dichloromethane; water; methanol / 3 h / -5 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid / 115 °C 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 3: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme

C26H33BrO8 → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane; water at -5 - 0℃; for 3h; Inert atmosphere;

17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione (56665-79-3) → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 2: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme

21-Chloro-17α-hydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione (116846-77-6) → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium iodide / N,N-dimethyl-formamide / 3 h / 60 °C 2: perchloric acid; 5,5-dibromohydantoin / water / 3 h / -5 °C 3: sodium sulfite; sodium hydroxide / water; methanol / 3 h / 10 °C View Scheme

Acetic acid 2-((8S,9R,10S,11S,13S,14S,16S,17R)-9-bromo-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester → 17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Conditions	Yield
With sodium hydroxide; sodium sulfite In methanol; water at 10℃; for 3h;

17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0) → betamethasone (378-44-9)

Conditions	Yield
With hydrogen fluoride In water; N,N-dimethyl-formamide at -15℃;	89%
With hydrogen fluoride

17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0) → 9β,11β-epoxy-16β-methylandrosta-1,4-diene-3,17-dione (1192715-48-2)

Conditions	Yield
With bithmuth(III) triflate hydrate In 1,4-dioxane at 80℃; chemoselective reaction;	45%

17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0) → dexamethasone (50-02-2)

Conditions	Yield
With hydrogen fluoride

Upstream product

• 116846-77-6 21-Chloro-17α-hydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione 
• 56665-79-3 17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione 
• 85650-69-7 C₂₆H₃₆O₉S 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 

Downstream Products

• 378-44-9 betamethasone 
• 4419-39-0 beclomethasone 
• 5534-18-9 beclomethasone 17-monopropionate 
• 5534-09-8 beclomethasone 17,21-dipropionate 
• 205105-83-5 (9β,11β,16β)-9,11-epoxy-17-hydroxy-16-methyl-21-(1-oxopropoxy)pregna-1,4-diene-3,20-dione 
• 50-02-2 dexamethasone 

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