GB936235A - Process for the manufacture of unsaturated steroids - Google Patents

Process for the manufacture of unsaturated steroids

Info

Publication number
GB936235A
GB936235A GB4317759A GB4317759A GB936235A GB 936235 A GB936235 A GB 936235A GB 4317759 A GB4317759 A GB 4317759A GB 4317759 A GB4317759 A GB 4317759A GB 936235 A GB936235 A GB 936235A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
steroids
esters
mesyloxy
acetoxy
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
GB4317759A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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
Priority claimed from CH6771058A external-priority patent/CH382735A/en
Priority claimed from CH6936959A external-priority patent/CH372298A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB936235A publication Critical patent/GB936235A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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
    • 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

D 9,11-Steroids are prepared by heating sulphonic acid esters of 11a -hydroxy-steroids with a lithium halide in a basic solvent under anhydrous conditions. An alkali metal or alkaline earth metal carbonate may also be present. Suitable solvents include bases such as pyridine and collidine and dialkyl formamides. Steroids of the androstane, pregnane, spirostane, cholestane or ergostane series may be used. Specified starting materials are the sulphonic acid esters of the following 11a -hydroxy steroids: testosterone with or without a 17a -methyl substituent and/or a D 1 double bond, progesterone, corticosterone and its 21-esters, hydrocortisone and its 21-esters, prednisolone and its 21-esters, and 11a :17a :21-trihydroxy- 16a -methylallopregnane-3:20-dione and the corresponding D 4, D 1 and D 1,4 analogues and 21-esters thereof, and 3b -acetoxy-11a -hydroxy-5a -spirostan. Esterifying acids include alkane sulphonic acids and benzene and substituted-benzene sulphonic acids. Examples are given and the preparation of 11a -mesyloxy-17a -methyl-testosterone, 11a -tosyloxy- and 11a -mesyloxy-17a -hydroxy-16a -methyl- 21-acetoxy-allopregnane - 3:20-dione, D 1:4-11a -mesyloxy- 16a -methyl-17a -hydroxy 21-acetoxy-pregnadiene-3:20-dione and 3b -acetoxy-11a -mesyloxy-5a -spirostan from the corresponding 11a -hydroxy steroids and the appropriate acid chlorides is also described. Specification 809,114 is referred to.
GB4317759A 1958-12-24 1959-12-18 Process for the manufacture of unsaturated steroids Expired GB936235A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6771058A CH382735A (en) 1958-12-24 1958-12-24 Process for the preparation of 16a-methyl-17a-hydroxy compounds of the allopregnan series
CH6936959A CH372298A (en) 1959-02-10 1959-02-10 Process for the preparation of 9,11-unsaturated steroids

Publications (1)

Publication Number Publication Date
GB936235A true GB936235A (en) 1963-09-04

Family

ID=25737924

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4317759A Expired GB936235A (en) 1958-12-24 1959-12-18 Process for the manufacture of unsaturated steroids

Country Status (1)

Country Link
GB (1) GB936235A (en)

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