54024-17-8

Usage

Uses

Used in Pharmaceutical Industry:
18-Methyl-11-methyleneestr-4-ene-3,17-dione is used as a key intermediate in the synthesis of Desogestrel (D296875), an oral contraceptive. Its role in the pharmaceutical industry is crucial for the development of effective birth control medications, as it contributes to the formation of the final product with desired hormonal properties.
In the preparation of Desogestrel, 18-Methyl-11-methyleneestr-4-ene-3,17-dione acts as a precursor molecule, undergoing further chemical reactions to yield the final contraceptive compound. This process highlights the importance of 18-Methyl-11-methyleneestr-4-ene-3,17-dione in the pharmaceutical industry, as it enables the production of a widely used and effective oral contraceptive.

Upstream product

• 56294-43-0 13-ethyl-11-methylenegon-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) 
• 220332-82-1 (+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one 
• 1433398-43-6 [(17,17-(2,2-dimethyl)propane1,3-dioxy)]-13β-ethyl-11α-hydroxy-3-methoxygona-1,3,5-triene 
• 1433398-55-0 17,17-(2,2-dimethyl)propane-1,3-dioxyl-13β-ethyl-11-oxo-3-methoxy-gona-1,3,5-triene 
• 1433398-67-4 [(17,17-(2,2-dimethyl)propane-1,3-dioxyl)]-13β-ethyl-11β-hydroxy-3-methoxy-11-α-trimethylsilyl-methylgona-1,3,5(10)-triene 
• 7443-72-3 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol 
• 1433398-79-8 C₂₉H₄₈O₄Si 
• 38393-52-1 (13S,14S)-13-ethyl-3-methoxy-6,7,11,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one 
• 1574323-07-1 C₂₁H₃₀O₄ 
• 168131-50-8 18a-methylestr-5-ene-3,11,17-trione cyclic 3-(1,2-ethanediyl acetal) 
• 59860-72-9 3,3:17,17-bis[1,2-ethenediylbis(oxy)]-11β-hydroxyestr-5-en-18-oic acid γ-lactone 
• 59017-10-6 13-ethyl-11β-hydroxygon-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) 
• 184778-59-4 13β-ethyl-11α-hydroxygon-5-ene-3,17-dione-3,17-diethylene ketal 
• 100071-89-4 18a-homoestr-5-ene-3,11,17-trione cyclic 3,17-bis(1,2-ethanediyl acetal) 

Downstream Products

• 54024-21-4 11-methylene-18a-homo-estr-4-en-17-one 
• 54024-22-5 desogestrel 

Relevant academic research and scientific papers

A partial synthesis of 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (desogestrel) based upon intramolecular oxidation of an 11β-hydroxy-19-norsteroid to the 18->11β-lactone

A partial synthesis of the 13-ethyl-18-norsteroid desogestrel is reported.The key step in the synthesis is the intramolecular oxidation of 11β-hydroxyestr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) 3 with Pb(OAc)4 and iodine to 3,3:17,17-bis-11β-hydroxyestr-5-en-18-oic acid γ-lactone 2.The 13-COOH group was then converted into a 13-ethyl group by a Grignard reaction with methylmagnesium bromide followed by Wolff-Kishner reduction of the 13-acetyl group thus formed.

PROCESS FOR PREPARING 11 -METHYLENE-18-METHYL-ESTR-4-EN-3, 17- DIONE, USEFUL AS INTERMEDIATE COMPOUND FOR THE SYNTHESIS OF MOLECULES HAVING A PHARMACOLOGICAL ACTIVITY

There is described a process for the industrial synthesis of 11-methylene-18- methyl-estr-4-en-3, 17-dione, a compound having the structure formula (I) depicted below: (Formula I) (I) useful as intermediate compound in the synthesis of the progestin compounds Desogestrel and Etonogestrel.

METHODS FOR THE PREPARATION OF ETONOGESTREL AND DESOGESTREL

Described herein is a process for the synthesis of etonogestrel and desogestrel and intermediates used to form etonogestrel and desogestrel.

Enantioselective total synthesis of the oral contraceptive desogestrel by a double heck reaction

A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.

Synthesis of 13-ethyl-17-hydroxy-11-methylene-18,19-dinor-17α-pregn-4- en-20-yn-3-one (3-oxo desogestrel)

A synthesis of the steroid hormone, 3-keto-desogestrel (1), with the total yield of 10% starting from d-13β-ethyl-3-methoxy-gona-1,3,5(10),8- tetraen-18β-ol (3) is described.

An improved synthesis of 13β-ethyl-11-methylenegon-4-en-3,17-dione

An improved synthesis of 13β-ethyl-11-methylenegon-4-en-3,17-dione with the total yield of 57% starting from 13β-ethyl-11α-hydroxy-gon-4-ene-3,17- dione is described.