GB939510A - Process for the manufacture of pregnadienes - Google Patents

Process for the manufacture of pregnadienes

Info

Publication number
GB939510A
GB939510A GB4393659A GB4393659A GB939510A GB 939510 A GB939510 A GB 939510A GB 4393659 A GB4393659 A GB 4393659A GB 4393659 A GB4393659 A GB 4393659A GB 939510 A GB939510 A GB 939510A
Authority
GB
United Kingdom
Prior art keywords
dibromide
hydrogen bromide
preparation
pregnadienes
hydrogen
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
GB4393659A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB939510A publication Critical patent/GB939510A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (a) a process for the preparation of D 1:4-pregnadienes of the formula <FORM:0939510/IV(a)/1> (wherein R and R1 are free or esterified hydroxyl groups but are not sulphonic acid ester groups) in which the corresponding allopregnane saturated in A ring is brominated to give a 2,2-dibromide, this is rearranged to the 2,4-dibromide by means of hydrogen bromide, and hydrogen bromide is eliminated from the 2,4-dibromide; and (b), as new chemical compounds, the 2,4-dibromo intermediates of this process. The elimination of hydrogen bromide is advantageously effected with a base such as collidine or dimethylformamide and lithium chloride and/or lithium carbonate, or by the action of a hydrazine derivative. To ensure rapid and complete rearrangement to the 2,4-dibromide, hydrogen halide is advantageously added to the solution at the beginning of the bromination, which is performed in the conventional way with molecular bromine in a solvent. Examples describe the preparation of D 1:4-16a -methyl- 21-acetoxypregnadiene-11a :17a -diol -3:20-dione and the 11a -acetate thereof. An extensive list of esterifying acids, including organic mono- and di-carboxylic acids, phosphoric acid and sulphuric acid, is also provided. Specifications 832,244, 924,251, 924,252 and 933,959 are referred to.
GB4393659A 1959-02-10 1959-12-24 Process for the manufacture of pregnadienes Expired GB939510A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH6936659A CH405306A (en) 1959-02-10 1959-02-10 Process for the preparation of pregnadiene compounds

Publications (1)

Publication Number Publication Date
GB939510A true GB939510A (en) 1963-10-16

Family

ID=4529447

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4393659A Expired GB939510A (en) 1959-02-10 1959-12-24 Process for the manufacture of pregnadienes

Country Status (2)

Country Link
CH (1) CH405306A (en)
GB (1) GB939510A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681409A (en) * 1969-02-11 1972-08-01 Merck Patent Gmbh 9{60 -fluoro-16-fluoromethyleneprednisolone-21-enanthate and process for the preparation thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681409A (en) * 1969-02-11 1972-08-01 Merck Patent Gmbh 9{60 -fluoro-16-fluoromethyleneprednisolone-21-enanthate and process for the preparation thereof

Also Published As

Publication number Publication date
CH405306A (en) 1966-01-15

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