GB445189A - The manufacture of unsaturated diketones related to the corpus luteum hormone - Google Patents

The manufacture of unsaturated diketones related to the corpus luteum hormone

Info

Publication number
GB445189A
GB445189A GB2536934A GB2536934A GB445189A GB 445189 A GB445189 A GB 445189A GB 2536934 A GB2536934 A GB 2536934A GB 2536934 A GB2536934 A GB 2536934A GB 445189 A GB445189 A GB 445189A
Authority
GB
United Kingdom
Prior art keywords
pregnenolone
oxidation
halogen
chromium trioxide
pregnendione
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
GB2536934A
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.)
Schering Kahlbaum AG
Original Assignee
Schering Kahlbaum AG
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 Schering Kahlbaum AG filed Critical Schering Kahlbaum AG
Priority to GB2536934A priority Critical patent/GB445189A/en
Publication of GB445189A publication Critical patent/GB445189A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pregnendiones are produced by oxidation of pregnenolones. The oxidation may be carried out on the pregnenolone itself, or the double bond may be first protected by saturation with halogen, for example, bromine, and the halogen removed after oxidation to regenerate the pregnendione. Examples in which direct oxidation is employed are: (1) Pregnenolone as obtained for instance according to the process described in Specification 443,964 is treated in glacial acetic acid with chromium trioxide at 15 DEG C. for 2 days. Instead of chromium trioxide, Beckmann chromic acid mixture can be used. (2) Pregnenolone is oxidized by fusion at about 300 DEG C. with \ba1/5\be of its weight of powdered copper oxide, or by shaking with lead dioxide in dilute hydrochloric acid. (3) Pregnenolone is treated with alkaline alcoholic hydrogen peroxide. Examples in which the double bond is protected by halogen are: (4) Brominated pregnenolone is shaken with aqueous acid permanganate, and the pregnendione isolated by the action of zinc dust in glacial acetic acid. (5) Brominated pregnenolone is oxidized in the cold with chromium trioxide, and debrominated by treatment with zinc dust.
GB2536934A 1934-09-03 1934-09-03 The manufacture of unsaturated diketones related to the corpus luteum hormone Expired GB445189A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2536934A GB445189A (en) 1934-09-03 1934-09-03 The manufacture of unsaturated diketones related to the corpus luteum hormone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2536934A GB445189A (en) 1934-09-03 1934-09-03 The manufacture of unsaturated diketones related to the corpus luteum hormone

Publications (1)

Publication Number Publication Date
GB445189A true GB445189A (en) 1936-04-03

Family

ID=10226552

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2536934A Expired GB445189A (en) 1934-09-03 1934-09-03 The manufacture of unsaturated diketones related to the corpus luteum hormone

Country Status (1)

Country Link
GB (1) GB445189A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2884417A (en) * 1952-12-17 1959-04-28 Merck & Co Inc 5, 6-dichloro pregnanes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2884417A (en) * 1952-12-17 1959-04-28 Merck & Co Inc 5, 6-dichloro pregnanes

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