GB838756A - Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds - Google Patents

Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds

Info

Publication number
GB838756A
GB838756A GB1522758A GB1522758A GB838756A GB 838756 A GB838756 A GB 838756A GB 1522758 A GB1522758 A GB 1522758A GB 1522758 A GB1522758 A GB 1522758A GB 838756 A GB838756 A GB 838756A
Authority
GB
United Kingdom
Prior art keywords
estr
cyan
ethoxy
ethylenedioxy
testosterone
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
GB1522758A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB1522758A priority Critical patent/GB838756A/en
Publication of GB838756A publication Critical patent/GB838756A/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 17-cyan-17-ol-estr-4 - en - 3 - one, 3 - ethoxy - 17 - cyan - 17 - ol-estr-3,5-diene, and 3-ethylenedioxy - 17 - cyan-17-ol-estr-5-ene and a process for the preparation of 17-alkyl- and 17-ethynyl-19-nor-testosterones of the general formula <FORM:0838756/IV (b)/1> wherein R represents an alkyl group containing 1 to 4 carbon atoms or an ethynyl group, by converting ester-4-en-3,17-dione into 17-cyano-17 - ol - estr - 4 - en - 3 - one, converting this compound into a 3-ethoxy-17-cyan-17-ol-estr-3,5 - diene or 3 - ethylenedioxy - 17 - cyan - 17 - ol - estr - 5 - ene, and converting the 3-ethoxy or 3-ethylenedioxy derivative into the desired 17-alkyl-or 17-alkynyl-19-nor-testosterone. The first step may be carried out using acetonecyanhydrin either alone or in alcoholic solution as the reagent to form a mixture of the 17a - and 17b -epimers. The second step may be carried out using either ethyl ortho-formate in the presence of an alcoholic solution of hydrochloric acid to form the 3-ethoxy derivative, or ethylene glycol to form the 3-ethylenedioxy derivative. Detailed examples are given.
GB1522758A 1958-05-12 1958-05-12 Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds Expired GB838756A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1522758A GB838756A (en) 1958-05-12 1958-05-12 Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1522758A GB838756A (en) 1958-05-12 1958-05-12 Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds

Publications (1)

Publication Number Publication Date
GB838756A true GB838756A (en) 1960-06-22

Family

ID=10055301

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1522758A Expired GB838756A (en) 1958-05-12 1958-05-12 Preparation of 17ª‡-homologues of 19-nor-testosterone and new intermediate compounds

Country Status (1)

Country Link
GB (1) GB838756A (en)

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