54024-17-8

Basic information

• Product Name: 18-Methyl-11-methyleneestr-4-ene-3,17-dione
• Synonyms: 18-Methyl-11-methyleneestr-4-ene-3,17-dione;Gon-4-ene-3,17-dione, 13-ethyl-11-Methylene-;(8S,9S,10R,14S)-13-Ethyl-11-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenan;Etonogestrel Related CoMpound A;(8S,9S,10R,14S)-13-Ethyl-11-Methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione;(8S,9S,10R,14S)-13-Ethyl-11-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phe
• CAS NO: 54024-17-8
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.41924
• Product Categories: API
• Mol File: 54024-17-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.11
• Vapor Pressure: 0-0Pa at 20-25℃
• CAS DataBase Reference: 18-Methyl-11-methyleneestr-4-ene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 18-Methyl-11-methyleneestr-4-ene-3,17-dione(54024-17-8)
• EPA Substance Registry System: 18-Methyl-11-methyleneestr-4-ene-3,17-dione(54024-17-8)

Safety Data

• Hazardous Substances Data: 54024-17-8(Hazardous Substances Data)

Usage

Uses

18-Methyl-11-methyleneestr-4-ene-3,17-dione is used in the preparation of Desogestrel (D296875), which is oral contraceptive.

Upstream product

• 196716-44-6 D-13β-Ethyl-11β-hydroxy-11α-methylgon-5-ene-3,11-dione-3,17-diethylene ketal 
• 220332-82-1 (+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one 
• 168131-50-8 18a-methylestr-5-ene-3,11,17-trione cyclic 3-(1,2-ethanediyl acetal) 
• 1574323-07-1 C₂₁H₃₀O₄ 
• 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) 
• 190507-48-3 (8S,9S,11S,13S,14S,17S)-17-Benzyloxy-13-ethyl-3-methoxy-11-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-11-ol 
• 190507-49-4 (8S,9S,11S,13S,14S,17S)-13-Ethyl-3-methoxy-11-methyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-11,17-diol 
• 190507-50-7 D-13β-ethyl-11β,17β-dihydroxy-11α-methylgon-4-en-3-one 
• 87834-69-3 17β-benzyloxy-D-13β-ethyl-3-methoxy-estra-1,3,5(10),9(11)-tetraene 
• 97996-45-7 17β-benzyloxy-D-13β-ethyl-3-methoxy-estra-1,3,5(10)-triene-11-one 
• 87834-70-6 17β-benzyloxy-D-13β-ethyl-11α-hydroxy-3-methoxy-estra-1,3,5(10)-triene 

Downstream Products

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

Relevant articles and documents

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.

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.

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.