54024-21-4

Basic information

• Product Name: 13b-Ethyl-11-methylenegon-4-en-17-one
• Synonyms: 13b-Ethyl-11-methylenegon-4-en-17-one;13-Ethyl-11-methylene-gon-4-en-17-one;Desogestrel InterMediates;Desogestrel EP IMpurity C;(8S,9S,10R,14S)-13-Ethyl-11-methylene-2,3,7,8,9,10,11,12,13, 14,15,16-dodecahydro-1H-cyclopenta[a;11-methylene-13-ethyl-gon-4-ene-17-one;(8S,9S,10R,14S)-13-Ethyl-11-methylene-2,3,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(6H)-one;(8S,9S,10R,14S)-13-Ethyl-11-methylene-2,3,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta
• CAS NO: 54024-21-4
• Molecular Formula: C₂₀H₂₈O
• Molecular Weight: 284.44
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 54024-21-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 99-1010C
• Boiling Point: 412.533 °C at 760 mmHg
• Flash Point: 177.856 °C
• Appearance: /
• Density: 1.051 g/cm³
• Refractive Index: 1.547
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 13b-Ethyl-11-methylenegon-4-en-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 13b-Ethyl-11-methylenegon-4-en-17-one(54024-21-4)
• EPA Substance Registry System: 13b-Ethyl-11-methylenegon-4-en-17-one(54024-21-4)

Safety Data

• Hazardous Substances Data: 54024-21-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Desogestrel intermediate

InChI:InChI=1/C20H28O/c1-3-20-12-13(2)19-15-7-5-4-6-14(15)8-9-16(19)17(20)10-11-18(20)21/h6,15-17,19H,2-5,7-12H2,1H3/t15-,16-,17?,19?,20-/m0/s1

Upstream product

• 220332-76-3 (+)-(1S,3aS,7aS)-hexahydro-1-(tert-butyldimethylsiloxy)-7a-ethyl-5-indanone 
• 196716-46-8 D-13β-Ethyl-11-methylenegon-4-en-17α-ol 
• 1822-00-0 trimethylsilylmethyllithium 
• 160683-93-2 18a-homo-estr-4-ene-11,17-dione 
• 163918-37-4 17,17-ethylenedioxy-18a-homo-estr-4-en-11-one 
• 1032401-75-4 (+)-17β-tert-butoxy-13β-ethyl-11-methylenegona-4-ene 
• 7370-08-3 11α,17β-Dihydroxy-18a-homo-estr-4-en-3-one 
• 160683-94-3 17,17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-en-11-one 
• 160683-91-0 3,3-ethylenedithio-18a-homo-estr-4-ene-11α,17β-diol 
• 160683-85-2 3-methoxy-18a-homo-estra-2,5(10)-diene-11α,17β-diol 
• 160683-92-1 18a-homo-estr-4-ene-11α,17β-diol 
• 196716-44-6 D-13β-Ethyl-11β-hydroxy-11α-methylgon-5-ene-3,11-dione-3,17-diethylene ketal 
• 196716-45-7 D-13β-Ethyl-3,3-ethylenedithio-11-methylenegon-4-ene-17α-ol 
• 100071-90-7 18-methyl-estra-4-en-3,11,17-trione 

Downstream Products

• 54048-10-1 etonogestrel 
• 54024-22-5 desogestrel 
• 110-54-3 hexane 

Relevant articles and documents

Synthesis of 13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (Desogestrel) and its Main Metabolite 3-Oxo-Desogestrel

A synthesis of the steroid hormone desogestrel (25) from the 18a-homo steroid 1 is described. 25 was transformed into 3-oxo-desogestrel (28) by allyl oxidation.

Intermediate used for synthesis of desogestrel, and preparation method and application thereof

The invention discloses an intermediate used for synthesis of desogestrel, and a preparation method and application thereof. The intermediate has a general chemical structural formula as described in the specification, wherein a substituting group R is selected from the group consisting of hydrogen, methyl or ethyl. The intermediate is prepared by subjecting a compound as shown in a formula 2 to selective protection reaction for a 3-carbonyl group by using dihydric alcohol, wherein the dihydric alcohol has a chemical structural formula as described in the specification, wherein R is selected from the group consisting of hydrogen, methyl or ethyl; and a reaction formula of the dihydric alcohol is described in the specification. The method for the synthesis of the desogestrel by employing the intermediate comprises a reaction route as described in the specification.

TOTAL SYNTHESIS OF ENANTIOPURE DESOGESTREL

The present invention relates to a total synthesis of desogestrel and derivatives thereof, and to intermediate compounds of this synthesis.