GB759705A - Cyclopentanophenanthrene derivatives and a method for the preparation thereof - Google Patents

Cyclopentanophenanthrene derivatives and a method for the preparation thereof

Info

Publication number
GB759705A
GB759705A GB6162/53A GB616253A GB759705A GB 759705 A GB759705 A GB 759705A GB 6162/53 A GB6162/53 A GB 6162/53A GB 616253 A GB616253 A GB 616253A GB 759705 A GB759705 A GB 759705A
Authority
GB
United Kingdom
Prior art keywords
diol
dione
pregnene
refluxed
dione acetate
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
GB6162/53A
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.)
American Syntex Inc Mexico
Original Assignee
American Syntex Inc Mexico
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 American Syntex Inc Mexico filed Critical American Syntex Inc Mexico
Publication of GB759705A publication Critical patent/GB759705A/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

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  • 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 D 1-allopregnene-, di4-pregnene- and D 1,4-pregnadiene-11a :17a -D ol-3:20-dione, their 11-esters, and processes for their preparation. The D 1-allopregnene-and D 1,4-pregnadiene compounds are prepared from allopregnane-11a :17a -diol-3:20-dione or an 11-ester thereof by selective bromination to yield the corresponding 2-bromo- and 2:4-dibromoderivatives, which are thereafter dehydrobrominated. The D 4 - pregnene compounds are obtained either (a) from allopregnane - 11a :17a - diol - 3:20 - dione or an 11-ester thereof, by polybrominating in at least the 2- and 4-positions of Ring A, treating the resultant bromo compound with sodium iodide in the presence of a lower aliphatic ketone to form the corresponding 2-iodo-D 4-pregnene, which is thereafter dehalogenated. In examples: (1) allopregnane-11a ,17a -diol-3,20-dione acetate is brominated in acetic acid containing HBr and the resulting 2-bromo derivative refluxed with 2,6-lutidine or collidine to yield D 1-allopregnene-11a ,17a -diol-3,20-dione acetate, which is saponified with alcoholic KOH to the free diol; (2) the 2-bromo derivative from (1) is dehydrobrominated by reaction with semicarbazide or 2,4-dinitrophenylhydrazine, treating the carbonyl derivative produced with pyruvic acid; (3) allopregnane-11a ,17a -diol-3,20-dione acetate is brominated as in (1), using 2 mols. bromine, to give the 2,4-dibromo derivative, which is refluxed with collidine giving D 1,f - pregnadiene - 11a ,17a - diol - 3,20 - dione acetate, subsequently saponified to the free diol; (4) the dibromo derivative from (3) is refluxed with NaI in acetone or methyl ethyl ketone, giving 2 - iodo - D 4 - pregnene - 11a ,17a - diol - 3,20-dione acetate, which is either refluxed with collidine (or lutidine or dimethylaniline), or treated with chromous chloride (or Raney nickel), yielding D 4-pregnene-11a ,17a -diol-3,20-dione acetate, subsequently saponified to the free diol; (5) 16a ,17a -oxido-allopregnan-11a -ol-3,20-dione acetate is brominated as in (3), giving 2,4,6 - tribromo - allopregnane - 11a ,17a -diol-3,20-dione acetate, which is refluxed with NaI in acetone and the resulting 2-iodo-16bromo - D 4 - pregnene - 11a ,17a - diol - 3,20-dione acetate refluxed with Raney nickel in ethanol to produce D 4-pregnene-11a ,17a -diol-3,20-dione acetate. Specifications 693,991 and 748,887 are referred to.
GB6162/53A 1952-03-07 1953-03-05 Cyclopentanophenanthrene derivatives and a method for the preparation thereof Expired GB759705A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX759705X 1952-03-07

Publications (1)

Publication Number Publication Date
GB759705A true GB759705A (en) 1956-10-24

Family

ID=19743006

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6162/53A Expired GB759705A (en) 1952-03-07 1953-03-05 Cyclopentanophenanthrene derivatives and a method for the preparation thereof

Country Status (1)

Country Link
GB (1) GB759705A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2981659A (en) * 1959-05-01 1961-04-25 Upjohn Co Method for the microbiological conversion of pregnane series steroids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2981659A (en) * 1959-05-01 1961-04-25 Upjohn Co Method for the microbiological conversion of pregnane series steroids

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