GB750918A - Improvements in or relating to the preparation of steroid substances - Google Patents

Improvements in or relating to the preparation of steroid substances

Info

Publication number
GB750918A
GB750918A GB2188553A GB2188553A GB750918A GB 750918 A GB750918 A GB 750918A GB 2188553 A GB2188553 A GB 2188553A GB 2188553 A GB2188553 A GB 2188553A GB 750918 A GB750918 A GB 750918A
Authority
GB
United Kingdom
Prior art keywords
acetate
keto
cortisone
dibromo
acetone
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
GB2188553A
Inventor
John Francis Oughton
Patrick Gadsden Jones
John Christoph Er Hamlet
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.)
GNRD Patent Holdings Ltd
Original Assignee
GNRD Patent Holdings Ltd
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 GNRD Patent Holdings Ltd filed Critical GNRD Patent Holdings Ltd
Priority to GB2188553A priority Critical patent/GB750918A/en
Publication of GB750918A publication Critical patent/GB750918A/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

D 4-3-Keto-steroids are prepared by reduction of D 4-2-iodo-3-keto-steroids with hydrogen iodide, preferably formed from excess alkali metal iodide and a non-oxidizing acid, particularly oxalic, tartaric or hydrochloric acid. The intermediate 2-iodosteroids are prepared from 3-keto-2 : 4-dibromoallosteroids by treatment with excess alkali metal iodide in an inert polar solvent, e.g. acetone, methyl ethyl ketone, tert.-butanol, tetrahydrofuran and methyl cyanide. In examples (1) 21-acetoxy- 2 : 4-dibromo - 17a - hydroxy - 3 : 11 : 20 - triketoallopregnane is refluxed with sodium iodide in acetone containing bromo acetone, oxalic acid is then added and mixture again refluxed, the solution is then concentrated, the iodine removed with thiosulphate, and cortisone 21-acetate extracted with ethyl acetate; (2) 17 : 21-diacetoxy - 2 : 4 - dibromo - 3 : 11 : 20 - triketo allopregnane is treated as in (1), effecting the removal of iodine from the ethyl acetate extract by treatment with zinc dust and acetic acid, after which cortisone diacetate is isolated on evaporation of the solvent; (3) as in (2) using 2 : 4-dibromo dihydro allocortisone acetate and acidifying with tartaric or hydrochloric acid to give cortisone acetate after purification. Specification 750,330 is referred to. Reference has been directed by the Comptroller to Specification 693,991.
GB2188553A 1953-08-07 1953-08-07 Improvements in or relating to the preparation of steroid substances Expired GB750918A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2188553A GB750918A (en) 1953-08-07 1953-08-07 Improvements in or relating to the preparation of steroid substances

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2188553A GB750918A (en) 1953-08-07 1953-08-07 Improvements in or relating to the preparation of steroid substances

Publications (1)

Publication Number Publication Date
GB750918A true GB750918A (en) 1956-06-20

Family

ID=10170449

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2188553A Expired GB750918A (en) 1953-08-07 1953-08-07 Improvements in or relating to the preparation of steroid substances

Country Status (1)

Country Link
GB (1) GB750918A (en)

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