ChemicalBook CAS DataBase List Megestrol acetate

Megestrol acetate synthesis

13synthesis methods

Product Name:Megestrol acetate
CAS Number:595-33-5
Molecular formula:C24H32O4
Molecular Weight:384.51

32634-95-0 Synthesis

17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate

32634-95-0
122 suppliers
$174.90/10mg

595-33-5
432 suppliers
$38.00/1g

Yield:-

Reaction Conditions:

with sodium acetate;palladium on activated charcoal;4-methylcyclohexene in ethanol;Heating / reflux;

Steps:

2.ii Process for Preparing Megestrol Acetate (2)

A suspension of one part 17α-acetoxy-6-methylenepregn-4-ene-3,20-dione, 0.1 part of sodium acetate and 0.06 part of palladium/carbon in 10 parts of ethanol and 0.01 part of 4-methyl-1-cyclohexene is heated at reflux with stirring, and the completeness of isomerization is determined by thin-layer chromatography. 1.5 parts of ethanol are added and the catalyst is filtered off under hot conditions, and is washed with ethanol. Combined wash liquors and filtrate are concentrated to 3 parts. For complete precipitation, 7.5 parts of water are added, and the crystals are removed and washed with water. After drying, 0.98 part of crude megestrol acetate is obtained, which is dissolved under hot conditions in 12 parts of methanol. The mixture is concentrated to a residual amount of bottoms of 2.4 parts, cooled and centrifuged. The moist substance is dissolved under hot conditions in 12 parts of methanol and, after concentration to a residual volume of 2 parts, cooled. The solid substance is removed, washed with methanol, and dissolved in 8 parts of acetone. After 0.05 part of activated carbon has been added, the mixture is heated to boiling, the activated carbon is filtered off and the filtrate is concentrated to a residual amount of bottoms of 1 part. The suspension is cooled, and the crystals are removed and washed with acetone. After drying, 0.85 part of megestrol acetate with a melting point of 217-220° C. and [α]_D²⁵=+11° (chloroform) is isolated. Content: 100.3% (HPLC).

References:

US2009/12321,2009,A1 Location in patent:Page/Page column 3

71-58-9 Synthesis