ES275012A1 - Process for the preparation of 10 -methyl steroids - Google Patents

Process for the preparation of 10 -methyl steroids

Info

Publication number
ES275012A1
ES275012A1 ES0275012A ES275012A ES275012A1 ES 275012 A1 ES275012 A1 ES 275012A1 ES 0275012 A ES0275012 A ES 0275012A ES 275012 A ES275012 A ES 275012A ES 275012 A1 ES275012 A1 ES 275012A1
Authority
ES
Spain
Prior art keywords
methyl
effected
group
methylation
protected
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
ES0275012A
Other languages
Spanish (es)
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of ES275012A1 publication Critical patent/ES275012A1/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
    • 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 10b -methyl-13b -n-propyl-gona-4,9(11)-dien-3-one derivatives of the general formula <FORM:1003085/C2/1> in which R represents the oxygen atom of a keto group, or a hydrogen atom and either a hydroxy group or an ester group derived from either a mineral acid or an organic carboxylic acid, and a process in which a 17b -acyloxy-13b -alkyl - 4,5 - seco - gon - 9 - ene - 3,5 - dione is protected at the 3-position, the 3-protected compound is subjected to methylation in the presence of an enolizing agent to effect methylation at the 10b -position and migration of the 9(10)-double bond to the 9(11)-position, the 3-protected keto group is liberated and the thus-freed ketonic compound is cyclized by alkali metal hydroxide into the corresponding 13b -alkyl - 17b - hydroxy - 10b - methyl - gona - 4,9(11)-dien-3-one. Protection of the 3-keto group may be effected by ketalization, e.g. with methyl-ethyl-dioxolan. Methylation may be effected with methyl iodide in the presence of potassium t.-amylate. Cyclization may be effected with potassium hydroxide in methanol. The 17b -hydroxy group in the so-obtained product may be oxidized to obtain the corresponding 17-keto compound with chromic anhydride in acetic acid, or esterified by an esterifying agent derived from either a mineral acid or an organic carboxylic acid. Specifications 979,892, 979,898 and 1,003,086 are referred to.
ES0275012A 1961-03-01 1962-02-28 Process for the preparation of 10 -methyl steroids Expired ES275012A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR854250A FR1366728A (en) 1961-03-01 1961-03-01 New gonan derivatives and their preparation process

Publications (1)

Publication Number Publication Date
ES275012A1 true ES275012A1 (en) 1962-05-01

Family

ID=8749899

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0275012A Expired ES275012A1 (en) 1961-03-01 1962-02-28 Process for the preparation of 10 -methyl steroids

Country Status (6)

Country Link
BE (1) BE614522A (en)
BR (1) BR6236810D0 (en)
CH (1) CH406200A (en)
ES (1) ES275012A1 (en)
FR (1) FR1366728A (en)
GB (2) GB1003085A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL92952A (en) * 1990-01-03 1994-06-24 Teva Pharma R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
BE614522A (en) 1962-08-28
BR6236810D0 (en) 1973-05-24
CH406200A (en) 1966-01-31
GB1003085A (en) 1965-09-02
GB1003086A (en) 1965-09-02
FR1366728A (en) 1964-07-17

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