GB806047A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB806047A
GB806047A GB18706/57A GB1870657A GB806047A GB 806047 A GB806047 A GB 806047A GB 18706/57 A GB18706/57 A GB 18706/57A GB 1870657 A GB1870657 A GB 1870657A GB 806047 A GB806047 A GB 806047A
Authority
GB
United Kingdom
Prior art keywords
reacting
alkyltestosterone
dehydro
enamine
carbon atoms
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
GB18706/57A
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 GB806047A publication Critical patent/GB806047A/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

The invention comprises a 9(11)-dehydro-17-alkyltestosterone represented by the formula <FORM:0806047/IV (b)/1> wherein R1 is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing from 1 to 12 carbon atoms and wherein R is a methyl or ethyl group, and the 3-pyrrolidyl enamines thereof, and the preparation thereof by (a) reacting an 11b -hydroxy-17-alkyltestosterone with N-bromacetamide and sulphur dioxide under anhydrous conditions and, if desired, reacting the product with the anhydride of an organic carboxylic acid containing 1-12 carbon atoms inclusive; or (b) reacting the 3-enamine of 4,9(11) - androstadiene - 3,17 - dione with an alkyl magnesium halide to produce the 3-enamine of a 9,11-dehydro-17-alkyltestosterone, hydrolysing the latter compound with aqueous alkali and reacting the product with the anhydride of an organic carboxylic acid containing 1-12 carbon atoms inclusive. As an alternative to (a) dehydration may be effected by means of p-toluenesulphonyl chloride followed by reaction with sodium formate. Examples describe the preparation of 9(11) - dehydro - 17 - methyltestosterone, the 3-pyrrolidyl enamine thereof and 17-esters thereof. Specifications 724,149 and 750,941 are referred to.
GB18706/57A 1955-08-08 1956-02-20 Improvements in or relating to steroids and the manufacture thereof Expired GB806047A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US806047XA 1955-08-08 1955-08-08

Publications (1)

Publication Number Publication Date
GB806047A true GB806047A (en) 1958-12-17

Family

ID=22158424

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18706/57A Expired GB806047A (en) 1955-08-08 1956-02-20 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB806047A (en)

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