GB491799A - Manufacture of derivatives of cyclopentano-polyhydrophenanthrene - Google Patents

Manufacture of derivatives of cyclopentano-polyhydrophenanthrene

Info

Publication number
GB491799A
GB491799A GB678037A GB678037A GB491799A GB 491799 A GB491799 A GB 491799A GB 678037 A GB678037 A GB 678037A GB 678037 A GB678037 A GB 678037A GB 491799 A GB491799 A GB 491799A
Authority
GB
United Kingdom
Prior art keywords
stands
acyloxy
acetoxypregnanone
progesterone
acetoxy
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
GB678037A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB678037A priority Critical patent/GB491799A/en
Publication of GB491799A publication Critical patent/GB491799A/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

Unsaturated polyhydroxy derivatives of cyclopentanopolyhydrophenanthrene are prepared from compounds of the general formula <FORM:0491799/IV/1> where Ac stands for an acyl residue, at least one R stands for acyloxy, the other R stands for hydrogen or acyloxy, and X stands for C = O, C = NH, CHOH, or CHNH2, by a process which comprises saponifying the acyloxy group at position 3, oxidizing to the corresponding 3-keto compound, halogenating, and removing hydrogen halide. In those compounds in which X does not stand for C = O, the product obtained as described above may be further treated by the usual methods to convert X into C = O. The application of the process of the invention to 3 : 12 diacetoxypregnanone-20 with the intermediate production of 12-acetoxyprogesterone and leading finally to 12-hydroxy-progesterone, has proved to be especially important. In an example dihydroxypregnanone-20 is esterified with acetic anhydride in the presence of pyridene to give 3 : 12-di-acetoxypregnanone, which is then partially saponified to 3-hydroxy-12-acetoxypregnanone. This is then oxidized with chromic acid to 12-acetoxypregnanedione-3 : 20, brominated to 12-acetoxy-4-bromopregnanedione-3 : 20, and dehalogenated by boiling with aqueous pyridine to give 12-acetoxy-progesterone, which may be saponified to the corresponding 12-hydroxyprogesterone. Specification 465,960 is referred to.
GB678037A 1937-03-08 1937-03-08 Manufacture of derivatives of cyclopentano-polyhydrophenanthrene Expired GB491799A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB678037A GB491799A (en) 1937-03-08 1937-03-08 Manufacture of derivatives of cyclopentano-polyhydrophenanthrene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB678037A GB491799A (en) 1937-03-08 1937-03-08 Manufacture of derivatives of cyclopentano-polyhydrophenanthrene

Publications (1)

Publication Number Publication Date
GB491799A true GB491799A (en) 1938-09-08

Family

ID=9820598

Family Applications (1)

Application Number Title Priority Date Filing Date
GB678037A Expired GB491799A (en) 1937-03-08 1937-03-08 Manufacture of derivatives of cyclopentano-polyhydrophenanthrene

Country Status (1)

Country Link
GB (1) GB491799A (en)

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