GB655983A - Production of 3-hydroxy-11-keto steroids - Google Patents

Production of 3-hydroxy-11-keto steroids

Info

Publication number
GB655983A
GB655983A GB6206/48A GB620648A GB655983A GB 655983 A GB655983 A GB 655983A GB 6206/48 A GB6206/48 A GB 6206/48A GB 620648 A GB620648 A GB 620648A GB 655983 A GB655983 A GB 655983A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
keto
keto steroids
steroids
hydroxy group
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
GB6206/48A
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.)
Research Corp
Original Assignee
Research Corp
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 Research Corp filed Critical Research Corp
Publication of GB655983A publication Critical patent/GB655983A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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

3-Hydroxy-11-keto steroids are obtained by converting 3(a )-hydroxy-12-keto steroids to the corresponding 3 : 12-dihydroxy-11-keto steroids by acylating the 3(a )-hydroxy group, brominating to give the two 11-bromo epimers, hydrolysing the bromo-keto esters to the two epimeric 3 : 11-dihydroxy-12-keto steroids which are isomerized by boiling with strong alkali to the corresponding 3 : 12-dihydroxy-11-keto steroids, differentially acylating the 3-hydroxy group to give the 3-acyloxy-12-hydroxy-11-keto steroids, replacing the 12-hydroxy group with halogen, replacing the halogen with hydrogen, and hydrolysing the ester group on the 3-hydroxy group to give the 3-hydroxy-11-keto steroid. The 3-hydroxy-12-keto steroids are represented by desoxycholic acid and its derivatives. Replacement of the 12-hydroxy group may be effected with phosphorus tribromide or trichloride and thionyl bromide or chloride. Reduction of the halogen to hydrogen may be effected with zinc dust and glacial acetic acid. Detailed examples are given.
GB6206/48A 1946-06-24 1948-02-27 Production of 3-hydroxy-11-keto steroids Expired GB655983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US655983XA 1946-06-24 1946-06-24

Publications (1)

Publication Number Publication Date
GB655983A true GB655983A (en) 1951-08-08

Family

ID=22063824

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6206/48A Expired GB655983A (en) 1946-06-24 1948-02-27 Production of 3-hydroxy-11-keto steroids

Country Status (1)

Country Link
GB (1) GB655983A (en)

Similar Documents

Publication Publication Date Title
GB655983A (en) Production of 3-hydroxy-11-keto steroids
GB1045979A (en) Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
GB946302A (en) Novel steroids and process for their manufacture
GB642489A (en) Production of chlorbutyl esters of carboxylic acids
GB843214A (en) Improvements in or relating to steroid compounds
GB609913A (en) Improvements in and relating to the preparation of derivatives of cholesterol
GB944718A (en) New steroid compounds and processes for their preparation
GB888974A (en) Steroids
GB935116A (en) New cyclopentanophenanthrene derivatives and processes for the production thereof
GB779188A (en) Manufacture of acids of the trisnorlanostane series and their derivatives
GB744804A (en) Improvements in or relating to the manufacture of acid halides of the vitamin a-series
GB899582A (en) New cyclopentanophenanthrene derivatives and process for the production thereof
GB931577A (en) Improvements in or relating to the manufacture of steroids
GB880363A (en) Improvements in or relating to steroid compounds
GB781423A (en) Steroid compounds
GB644399A (en) Improvements in or relating to the production of tertiary rosin alcohols
GB447756A (en) Improvements relating to the production of acid anhydrides
GB817382A (en) Improvements in or relating to steroids and the manufacture thereof
GB803656A (en) Dehydrocortical hormones
GB963964A (en) Improvements in or relating to the bromination of hecogenin and esters thereof
GB623754A (en) Improvements in or relating to dehydro-iso-androsterone and process of producing the same
GB716299A (en) Steroids
ES251602A1 (en) Steroid compounds
GB652944A (en) Process for the preparation of 24-ketocholesterol and its derivatives
GB865316A (en) Improvements in or relating to steroids and the manufacture thereof