6870-94-6

Basic information

• Product Name: Pregna-1,4-diene-3,20-dione,11,17-dihydroxy-6-methyl-, (6a,11b)-
• Synonyms: Pregna-1,4-diene-3,20-dione,11,17-dihydroxy-6-methyl-, (6a,11b)-;FluoroMetholone Related CoMpound A;11beta,17alpha-Dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione;NSC 125051;Methyl Prednisolone Intermediates;Methylprednisolone EP Impurity L;11β,17α-Dihydroxy-6α-methylpregna-1,4-diene-3,20-dione
• CAS NO: 6870-94-6
• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.4712
• EINECS: 1592732-453-0
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 6870-94-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 222-231℃
• Boiling Point: 530.3°C at 760 mmHg
• Flash Point: 288.6°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.84E-13mmHg at 25°C
• Refractive Index: 1.584
• PKA: 12.86±0.70(Predicted)
• CAS DataBase Reference: Pregna-1,4-diene-3,20-dione,11,17-dihydroxy-6-methyl-, (6a,11b)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pregna-1,4-diene-3,20-dione,11,17-dihydroxy-6-methyl-, (6a,11b)-(6870-94-6)
• EPA Substance Registry System: Pregna-1,4-diene-3,20-dione,11,17-dihydroxy-6-methyl-, (6a,11b)-(6870-94-6)

Safety Data

• Hazardous Substances Data: 6870-94-6(Hazardous Substances Data)

Usage

Uses

Deltamedrane is an impurity in the synthesis of Fluorometholone (F593145), a glucocorticoid; anti-inflammatory.

InChI:InChI=1/C22H30O4/c1-12-9-15-16-6-8-22(26,13(2)23)21(16,4)11-18(25)19(15)20(3)7-5-14(24)10-17(12)20/h5,7,10,12,15-16,18-19,25-26H,6,8-9,11H2,1-4H3

Synthetic route

Methylprednisolone (83-43-2) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
ueber mehrere Stufen;

methylprednisolone acetate (53-36-1) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6) + 11β-hydroxy-6α-methyl-1,4-androstadiene-3,17-dione (61919-52-6) + 6α-methylprednisone acetate

Conditions	Yield
Product distribution; Rate constant; Irradiation; radiolytic degradation;

C26H42O6 → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / tetrahydrofuran / pH 2 - 3 2: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h View Scheme

11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione (7055-53-0) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
With potassium dihydrogenphosphate; D-glucose In methanol; water for 50h;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: trimethyloxosulfonium bromide; orthoformic acid triethyl ester / 5 h 2: sodium tetrahydroborate / tetrahydrofuran / 12 h 3: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 4: magnesium / tetrahydrofuran / 4 h 5: sulfuric acid / tetrahydrofuran / pH 2 - 3 6: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h View Scheme

3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one (74332-34-6) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / tetrahydrofuran / 12 h 2: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 3: magnesium / tetrahydrofuran / 4 h 4: sulfuric acid / tetrahydrofuran / pH 2 - 3 5: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h View Scheme

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol (41870-77-3) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 2: magnesium / tetrahydrofuran / 4 h 3: sulfuric acid / tetrahydrofuran / pH 2 - 3 4: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h View Scheme

C25H38O7 → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran / 4 h 2: sulfuric acid / tetrahydrofuran / pH 2 - 3 3: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h View Scheme

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6) + acetic acid (64-19-7) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Stage #1: 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione With iodine; calcium oxide In methanol; dichloromethane Stage #2: acetic acid With potassium acetate In acetone at 45 - 50℃; for 2h;

Upstream product

• 41870-77-3 3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol 
• 74332-34-6 3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one 
• 1882-82-2 17-hydroxy-pregn-4-ene-3,11,20-trione 
• 7055-53-0 11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione 
• 53-36-1 methylprednisolone acetate 
• 83-43-2 Methylprednisolone 

Downstream Products

• 53-36-1 methylprednisolone acetate 

Relevant articles and documents

A methylprednisolone production process and production apparatus (by machine translation)

The invention discloses a methylprednisolone production device, including connected according to the procedure of the reaction, shui xifu, centrifugal filtration equipment, the concentrator, [...], biological fermentation tank, drying apparatus, the drying apparatus comprises an outer cylinder, the drying cylinder, the inner cylinder; the bottom surface of the outer cylinder is provided with a motor, the rotation of the motor shaft is provided with a exhaust fan blade, type impeller, vortex impeller; exhaust fan leaf is arranged on the bottom surface of the drying cylinder between the cylinder and the outer cylinder; drum type impeller is arranged on the drying cylinder between the cylinder and an inner cylinder; vortex impeller is arranged on the bottom of the inner drum; [...] is set with infrared heating in; on the inner end center provided with a feed port; the outer tube side wall comprises an inner wall and the outer wall; the inner wall and the outer wall of the annular cavity formed between the interlayer; outlet at upper end of the sandwich cavity is provided with an annular baffle plate; the baffle plate is provided with a vent; the upper end of the baffle is provided with a rotatable air purifies the link. This invention can reduce the methylprednisolone intermediate product in the production process of the preparation time, realize methylprednisolone rapid high-quality production. (by machine translation)