GB628259A - Manufacture of intermediates in the synthesis of adrenal cortical hormone - Google Patents

Manufacture of intermediates in the synthesis of adrenal cortical hormone

Info

Publication number
GB628259A
GB628259A GB21052/46A GB2105246A GB628259A GB 628259 A GB628259 A GB 628259A GB 21052/46 A GB21052/46 A GB 21052/46A GB 2105246 A GB2105246 A GB 2105246A GB 628259 A GB628259 A GB 628259A
Authority
GB
United Kingdom
Prior art keywords
diketo
treated
trihydroxypregnane
anhydrides
pyridine
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
GB21052/46A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB628259A publication Critical patent/GB628259A/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

3 : 11 - Diketo - 17(b ) : 20 : 21 - trihydroxypregnane is manufactured by treating a D 17,20-3 : 11 - diketo - 21 - acyloxypregnene with osmium tetroxide, preferably in the presence of a tertiary amine, and hydrolysing the resulting osmate. The product may be treated with an acylating agent, preferably the anhydride of an aliphatic acid containing 6 carbon atoms or less, to produce a 3 : 11-diketo-17(b )-hydroxy - 20 : 21 - diacyloxypregnane. In an example, D 17,20 - 3 : 11 - diketo - 21 - acetoxypregnane is treated in ether with osmium tetroxide and pyridine and the product is refluxed with sodium sulphite in aqueous alcoholic solution to form 3 : 11 - diketo-17(b ) : 20 : 21 - trihydroxypregnane, which is treated with acetic anhydride and pyridine to give the 20 : 21-diacetate. Additional acylating agents specified are the anhydrides of propionic, butyric, valeric, caproic and capric acids. The Specification as open to inspection under Sect. 91 comprises also a reference to the use of carboxylic acids in complete or partial replacement of the anhydrides in the esterification step. This subject-matter does not appear in the Specification as accepted.
GB21052/46A 1945-07-14 1946-07-13 Manufacture of intermediates in the synthesis of adrenal cortical hormone Expired GB628259A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US628259XA 1945-07-14 1945-07-14

Publications (1)

Publication Number Publication Date
GB628259A true GB628259A (en) 1949-08-25

Family

ID=22045074

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21052/46A Expired GB628259A (en) 1945-07-14 1946-07-13 Manufacture of intermediates in the synthesis of adrenal cortical hormone

Country Status (1)

Country Link
GB (1) GB628259A (en)

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