GB739597A - Steroid ketals - Google Patents

Steroid ketals

Info

Publication number
GB739597A
GB739597A GB7777/53A GB777753A GB739597A GB 739597 A GB739597 A GB 739597A GB 7777/53 A GB7777/53 A GB 7777/53A GB 777753 A GB777753 A GB 777753A GB 739597 A GB739597 A GB 739597A
Authority
GB
United Kingdom
Prior art keywords
diketals
diketal
hydroxyprogesterone
diol
ether
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
GB7777/53A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB739597A publication Critical patent/GB739597A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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

The invention comprises 11b -hydroxypro-gesterone - 3 : 20 - diketals of the formula <FORM:0739597/IV (b)/1> wherein R is hydrogen or an alkyl radical containing from one to six carbon atoms, inclusive, and n is one or two, provided that the total number of carbon atoms in the polymethylenedioxy residue does not exceed 8, and also a process for their preparation which comprises treating the corresponding 11-keto-3 : 20-diketal with a reducing agent, classified as a mixed metal hydride, or hydrogen in the presence of a hydrogenation catalyst. The reaction is conducted in an inert solvent, e.g. ether, benzene, tetrahydrofuran and petroleum ether, and when using a mixed hydride, e.g. lithium aluminium hydride, lithium borohydride or sodium borohydride, the reaction product is hydrolysed with water. In examples (1) 11b -hydroxyprogesterone 3 : 20 - ethylene glycol diketal is prepared from the corresponding 11-keto compound by reduction with lithium aluminium hydride in ether or benzene. Other examples describe the formation of the corresponding 11b - hydroxy - 3 : 20 - diketals in which the polymethylenedioxy residue is derived from propane - 1 : 2 or 1 : 3 - diol; butane - 1 : 3-diol and octane-1 : 2-diol. (2) 11b -hydroxyprogesterone-3 : 20-ethylene glycol diketal is also prepared using sodium borohydride in aqueous isopropanol, and lithium borohydride in aqueous ethanol as the reducing agents. A further list of other 11b -hydroxyprogesterone-3 : 20-diketals is provided. Specification 734,805 is referred to.
GB7777/53A 1952-03-20 1953-03-20 Steroid ketals Expired GB739597A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US739597XA 1952-03-20 1952-03-20

Publications (1)

Publication Number Publication Date
GB739597A true GB739597A (en) 1955-11-02

Family

ID=22116849

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7777/53A Expired GB739597A (en) 1952-03-20 1953-03-20 Steroid ketals

Country Status (1)

Country Link
GB (1) GB739597A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3143559A (en) * 1962-10-03 1964-08-04 Olin Mathieson 12alpha-lower alkyl steroids and their method of preparation
US3166550A (en) * 1962-07-27 1965-01-19 Upjohn Co Process for 14alpha-methyl-11-ketoprogesterone and intermediates therefor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3166550A (en) * 1962-07-27 1965-01-19 Upjohn Co Process for 14alpha-methyl-11-ketoprogesterone and intermediates therefor
US3143559A (en) * 1962-10-03 1964-08-04 Olin Mathieson 12alpha-lower alkyl steroids and their method of preparation

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