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

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

• 160683-95-4 11-methylene-17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-ene 
• 196716-46-8 D-13β-Ethyl-11-methylenegon-4-en-17α-ol 
• 54024-20-3 (+)-13β-ethyl-11-methylenegona-4-en-17β-ol 
• 220332-76-3 (+)-(1S,3aS,7aS)-hexahydro-1-(tert-butyldimethylsiloxy)-7a-ethyl-5-indanone 
• 220332-77-4 (+)-(1S,3aS,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxyindane 
• 220332-82-1 (+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one 
• 220332-79-6 11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17β-ol 
• 54024-19-0 (+)-13β-ethyl-3,3-ethylenedithio-11-methylenegona-4-en-17β-ol 
• 161640-05-7 17β-(tert-butyldimethylsiloxy)-13-ethyl-11-methylene-3-methoxygona-1,3,5(10)-triene 
• 220332-78-5 (+)-(1S,3aS,4S,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxy-4-(2-(3-methoxyphenyl)ethyl)indane 
• 220332-80-9 17β-(tert-butyldimethylsiloxy)-11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraene 
• 54024-17-8 13β-ethyl-11-methylenegon-4-en-3,17-dione 
• 54024-18-9 13-ethyl-11-methylenegon-4-ene-3,17-dione cyclic 3-(1,2-ethanediyl dithioacetal) 
• 160683-93-2 18a-homo-estr-4-ene-11,17-dione 

Downstream Products

• 54024-22-5 desogestrel 
• 54048-10-1 etonogestrel 
• 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.

PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF 11-METHYLENE STEROIDS

The invention relates to a process for the preparation of 11 -methylene steroids through selective olefination of the ketone at position 11. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as Etonogestrel and Desogestrel.

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.

Desogestrel and its new process for preparation of the intermediate compounds

The invention relates to a preparation process for desogestrel and a novel intermediate compound thereof. In the prior art, 11-bit methylene is introduced through a wittig reaction in the preparation process of desogestrel, and a large quantity of environmental pollutants are produced in the reaction. In the preparation process for desogestrel and the novel intermediate compound thereof provided by the invention, the 11-bit methylene is introduced through an addition reaction, so that the problem of excessive discharge of pollutants is solved, reaction time is shortened, yield is increased, and industrial production is facilitated.

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.

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.

PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF STEROIDS WITH A PROGESTOGEN ACTIVITY

The present invention relates to a new process of synthesis and to some new intermediates for the preparation of steroids with progestogen activity, more particularly, for the preparation of Desogestrel of formula (I). Said process is characterized by the regioselective reduction of the compound of formula (II) to give the intermediate of formula (III).

A short enantioselective total synthesis of the third-generation oral contraceptive desogestrel

Desogestrel (1) has been synthesized enantioselectively by a 14-step process from the known and readily available precursor 3, as outlined in Chart 2. At the heart of this process is the short, convergent, and stereocontrolled method for forming the tetracyclic ring system and the critical 11-exomethylene function, that is, the sequence of steps 6 → 8 → → 12. All steps of the synthesis proceed in good yield.

Steroid intermediate products and method of their production

The invention is directed to novel steroid intermediate products of general formula I STR1 The steroid intermediate products which can be isolated according to the invention are suitable for the synthesis of 13-ethyl-11-methylene-18,19-bisnor-17α-pregn-4-en-20-in-17-ol (desogestrel). Further, processes for producing the steroid intermediate products of general formula I are described. The olefination of the 11-oxo steroids is carried out under the influence of ultrasound.