Basic information Safety Supplier Related

16α-Methyl-11-oxo Prednisolone

Basic information Safety Supplier Related

16α-Methyl-11-oxo Prednisolone Basic information

Product Name:
16α-Methyl-11-oxo Prednisolone
Synonyms:
  • Dexamethasone EP Impurity J
  • 16α-Methyl-11-oxo Prednisolone
  • Dexamethasone Impurity 10(Dexamethasone EP Impurity J)
  • (8S,9S,10R,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
  • (8S,9S,10R,13S,14S,16R,17R)
  • Dexamethasone impurity 4/Dexamethasone EP Impurity J
  • Pregna-1,4-diene-3,11,20-trione, 17,21-dihydroxy-16-methyl-, (16α)-
  • (8S,9S,10R,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione
CAS:
2036-77-3
MF:
C22H28O5
MW:
372.45
Product Categories:
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
Mol File:
2036-77-3.mol
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16α-Methyl-11-oxo Prednisolone Chemical Properties

Melting point:
197-199°C
Boiling point:
574.4±50.0 °C(Predicted)
Density 
1.28±0.1 g/cm3(Predicted)
storage temp. 
Refrigerator
solubility 
Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
12.38±0.70(Predicted)
color 
White to Off-White
Major Application
pharmaceutical small molecule
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16α-Methyl-11-oxo Prednisolone Usage And Synthesis

Uses

A 16α-substituted Prednisolone as potent topical antiinflammatory agent.

Synthesis

1) Add 5.0 g of pregnane-1,4,16-triene-3,11,20-trione (compound (I-1)) with 0.02 times copper bromide dimethyl sulfide, 1.2 times trimethylchlorosilane, 2 times hexamethylphosphorotriamine to 60 ml of tetrahydrofuran, and slowly add 1.2 times methylmagnesium bromide dissolved in the tetrahydrofuran to carry out the Grignard reaction, the temperature of the reaction is -30??-20??. The reaction was protected by passing N2, and at the end of the reaction it was diluted with water, separated and dried to obtain the Grignard product (compound (II-1)); 2) React the above Grignard with 3 times potassium bicarbonate and 1.5 times m-chloroperoxybenzoic acid in dichloromethane at a reaction temperature of -30 to -25??C, and react until complete. The solution pH was adjusted to 1 with hydrochloric acid, concentrated under reduced pressure, cooled, separated and dried to obtain the compound dexamethasone EP impurity J(III-1), total yield 78.2%.

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