GB739139A - Manufacture of 17-hydroxy-20-ketosteroids - Google Patents

Manufacture of 17-hydroxy-20-ketosteroids

Info

Publication number
GB739139A
GB739139A GB29588/53A GB2958853A GB739139A GB 739139 A GB739139 A GB 739139A GB 29588/53 A GB29588/53 A GB 29588/53A GB 2958853 A GB2958853 A GB 2958853A GB 739139 A GB739139 A GB 739139A
Authority
GB
United Kingdom
Prior art keywords
acetate
pregnene
diol
dione
iodo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB29588/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB739139A publication Critical patent/GB739139A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

17 - Hydroxy - 20 - keto - steroids are prepared by reacting a 16 : 17-oxido-20-keto-steroid with a salt of hydrogen iodide and an organic carboxylic or sulphonic acid, and the 16-iodo-17-hydroxy-20-keto-steroid thus produced is catalytically reduced to eliminate the 16-iodo substituent. The reaction may be carried out in an inert solvent in which the salt of hydrogen iodide in soluble e.g. low molecular weight alcohols, dioxane or ketones such as acetone, also in admixture with water. Suitable organic acids are lower aliphatic carboxylic acids such as formic, acetic and propionic acids, and p-toluene sulphonic acid. Alkali and alkaline earth metal iodides may be used in the reaction, e.g. sodium, potassium and calcium iodides. Reactants referred to are the 16 : 17-oxido derivatives of D 5 - pregnene - 3b - ol - 20 - one and the acetate thereof, D 4 - pregnene - 21 - ol - 3 : 20-dione acetate, progesterone, D 5 - pregnene-3b : 21 - diol - 20 - one - diacetate, allopregnane-3b : 21 - diol - 20 - one diacetate, pregnane-3a : 21 - diol - 20 - one diacetate, pregnane-3a - ol - 20 - one acetate, allopregnane - 3b -ol - 20 - one acetate, D 4 - pregnane - 11a - ol-3,20 - dione and pregnane - 3a : 21 - diol-11 : 20 - dione - 21 - acetate. In the examples, 16 - iodo - D 5 - pregnene - 3b : 17a - diol - 20-one and the 3b -acetate thereof, 16-iodo-D 4-pregnene - 17a : 21 - diol - 3 : 20 - dione - 21-acetate, 16 - iodo - 17a - hydroxy - progesterone, D 5 - pregnene - 3b : 17a - diol - 20 - one and the 3b - acetate thereof, D 4 - pregnene-17a : 21 - diol - 3 : 20 - dione - 21 - acetate and 17a -hydroxyprogesterone are prepared. A dibromo-steroid of the formula <FORM:0739139/IV (b)/1> is obtained by treating 16 : 17-oxido-D 4-pregnene - 3b - ol - 20 - one acetate with hydrogen bromide.
GB29588/53A 1952-10-25 1953-10-26 Manufacture of 17-hydroxy-20-ketosteroids Expired GB739139A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE739139X 1952-10-25

Publications (1)

Publication Number Publication Date
GB739139A true GB739139A (en) 1955-10-26

Family

ID=6642970

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29588/53A Expired GB739139A (en) 1952-10-25 1953-10-26 Manufacture of 17-hydroxy-20-ketosteroids

Country Status (1)

Country Link
GB (1) GB739139A (en)

Similar Documents

Publication Publication Date Title
GB739139A (en) Manufacture of 17-hydroxy-20-ketosteroids
GB1015396A (en) Steroid compounds
GB820779A (en) Cyclopentanophenanthrene derivatives
SU488406A3 (en) Method for producing 2,2-dimethyl steroids
GB753091A (en) Manufacture of a steroid hormone intermediate
GB814879A (en) Steroid compounds and the preparation thereof
GB722594A (en) Improvements in the manufacture of cellulose esters
US2038609A (en) Compounds containing a mercaptide group and method of producing same
GB796768A (en) Manufacture of derivatives of 5-pregnene-3,17ª‡-diol-20-ones
US2973374A (en) Process for the production of delta4-19-norpregnene-21-ol-3, 11, 20-triones
US2743287A (en) Hydroxyl compounds of the steroid series and process of making same
GB845442A (en) Manufacture of steroid compounds
GB889311A (en) Androstenol derivatives
GB960737A (en) 16ª‡,17ª‡-oxido steroids
GB881372A (en) Preparation of steroid compounds
GB747271A (en) Oxytetracycline diacetate
GB795452A (en) Pregnadiene derivatives
GB949843A (en) Cyclopentanophenanthrene derivatives and process for their preparation
GB746825A (en) Manufacture of cyclopentanopolyhydrophenanthrene compounds
GB922018A (en) 6ú·-and 6ªâ-fluoro-21-methyl-í¸-pregnene-17ú·, 21-diol-3, 20-dione-21-esters and preparation thereof
GB795454A (en) Steroid compounds
GB805585A (en) Steroid compounds
GB736817A (en) Improvements in or relating to reduction of 3-keto steroids to 3a-hydroxy steroids
GB991475A (en) Novel steroid compounds and processes for their production
GB738629A (en) Improvements relating to new 11-keto compounds of the androstene series and the preparation thereof