20380-17-0

Upstream product

• 106342-08-9 21-p-toluenesulfonate of 17α,21-dihydroxy-4-pregnene-3,20-dione 
• 132950-03-9 17α-hydroxy-3-(N-morpholinyl)pregna-3,5-dien-20-one 
• 2827-40-9 21-bromo-3β,17α-dihydroxy-5-pregnen-20-one 
• 434-03-7 levonorgestrel 
• 63973-94-4 17α-hydroxy-20-methoxypregna-4,20-diene-3-one 
• 152-58-9 Cortexolone 
• 107222-65-1 17α-(Bromethinyl)-17β-(trichloracetoxy)-4-androsten-3-on 
• 95716-48-6 17α-(Bromethinyl)-17β-(trifluoracetoxy)-4-androsten-3-on 
• 107222-62-8 17α-Ethinyl-17β-(trichloracetoxy)-4-androsten-3-on 
• 95716-47-5 17α-(Bromethinyl)-17β-(nitrooxy)-4-androsten-3-on 
• 65851-76-5 17α-ethynyl-17β-nitro-oxy-4-androsten-3-one 
• 85639-42-5 17α-ethynyl-17β-trifluoroacetoxy-androst-4-en-3-one 
• 387-79-1 17-Hydroxypregnenolone 
• 80134-08-3 21-Brom-17-(formyloxy)-4-pregnen-3,20-dion 

Downstream Products

• 640-87-9 cortexolone 21-acetate 
• 152-58-9 Cortexolone 
• 114967-86-1 α-(17α-Hydroxy-4-pregnene-3,20-dion-21-yl-21-thio)propionic acid 
• 114967-87-2 β-(17α-Hydroxy-4-pregnene-3,20-dion-21-yl-21-thio)propionic acid 
• 434-03-7 levonorgestrel 

Relevant academic research and scientific papers

Efficient Synthesis of the Corticosteroid Side-chain from 17-Ketones

Steroidal 17-ketones react smoothly with diethyl α-isocyanoethyl phosphonate to give, after suitable oxidative and hydrolytic reactions, the dihydroxy-acetone side-chain of corticosteroids in high yield.

An efficient hemisynthesis of 20- and 21-[13C]-labeled cortexolone: A model for the study of skin sensitization to corticosteroids

A method is described for the synthesis of isotopomers of cortexolone from the commercially available andros-4-ene-3, 17dione. The strategy is based on the use of K13CN for labeling at position 20 and of 13CH 3Mgl, generated in situ, for labeling at position 21. Because of the early introduction of the [13C] labeling, our efforts aimed at reproducible experimental procedures giving high yields with respect to the isotope containing precursors. During the development of this hemisynthesis, we noted that judicious choice of protective groups was essential as this could lead not only to mixtures or unstable intermediates but also influence considerably the output of reactions.

Process for the preparation of 21-bromo-4-pregnene-3,20-dione derivatives

A process is disclosed for the preparation of 21-bromo-4-pregnene-3,20-dione derivatives of general Formula I STR1 wherein R1 is a hydrogen atom, a hydroxy group or an alkanoyl group of up to 6 carbon atoms, R2 symbolizes a hydrogen atom or a methyl group, or wherein R1 and R2 jointly mean an isopropylidenedioxy group, wherein R3 is a hydrogen atom, a fluorine atom or a methyl group, V is a methylene group or ethylene group, X is a hydrogen atom, a fluorine atom or a chlorine atom, and Y is a methylene group, a hydroxymethylene group or a carbonyl group.

17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).

New Preparation and Controlled Alkaline Hydrolysis of 21-Bromo-20-ketopregnenes. A Facile Synthesis of Deoxycorticoids

Syntheses of deoxycorticoids 7b, 8b, and 9b are described.Treatment of 20-oxo steroid 1 with 3 mol equiv of CuBr2 in MeOH in the presence or absence of pyridine gave the 21-bromide 4a or the 17α-methoxide 2 in high yields, respectively.When 6 mol equiv of the brominating reagent was used in the absence of pyridine, the 21-bromo-17α-methoxide 5a was formed. 17α-hydroxy 20-ones 3 could be similarly converted to the 21-bromides 6a and 6b.Oxidation of 4a, 5a, and 6a with CrO3 and subsequent isomerization of a double bond at C-5 with acid gave the corresponding 4-ene-3-ones 7a, 8a, and 9a, of which 7a and 9a were efficiently hydrolized to 7b and 9b under controlled conditions with a K2CO3-H2O-acetone system.On the other hand, 8a was converted to 8b by reaction with NaOCH3 in MeOH.

Cyanohydrin process

Using cyanohydrin intermediates, 17-keto steroids are transformed to corticoids and 17α-acyl progesterones.

Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes

This invention discloses a general process for the production of corticoids from androstenes. This invention provides an economically viable alternative synthesis of 17α-hydroxyprogesterones and the corticoids.