GB1478679A - Electrolytic reduction of aromatic steroids - Google Patents

Electrolytic reduction of aromatic steroids

Info

Publication number
GB1478679A
GB1478679A GB31660/74A GB3166074A GB1478679A GB 1478679 A GB1478679 A GB 1478679A GB 31660/74 A GB31660/74 A GB 31660/74A GB 3166074 A GB3166074 A GB 3166074A GB 1478679 A GB1478679 A GB 1478679A
Authority
GB
United Kingdom
Prior art keywords
methoxy
alkali metal
metal salt
estratetraen
estradiene
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
GB31660/74A
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.)
Bayer Pharma AG
Original Assignee
Schering 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 AG filed Critical Schering AG
Publication of GB1478679A publication Critical patent/GB1478679A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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
    • C07J1/0051—Estrane derivatives
    • C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/008—Ketals at position 17
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/25—Reduction

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Steroid Compounds (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Abstract

1478679 Electrolytic reduction of #<SP>1,3,5(10)</SP>- to #<SP>2</SP>'<SP>5(10)</SP>-steroids SCHERING AG 17 July 1974 [18 July 1973] 31660/74 Heading C2U [Also in Division C7] #<SP>2</SP>'<SP>5(10)</SP>-Steroids containing an etherified hydroxy group in the 3-position are prepared from #<SP>1,3,5(10)</SP>- steroids containing the same group in the 3-position by electrolysis in liquid ammonia in either (a) a divided cell in the presence of an alkali metal salt of a strong acid (of pK < 5) or (b) an undivided cell in the presence of an alkali metal salt of a weak acid (of pK value 5-32). The strong acid salt may, for example, be a halide, tetrafluoroborate, sulphate or perchlorate and the weak acid salt may for example be an alkali metal salt of aniline, hydrazine, alcohol or water. The undivided cell may also contain an alkali metal salt of a strong acid. In examples estrone methyl ether is reduced to 3 - methoxy - #<SP>2</SP>'<SP>5(10)</SP> - estradien - 17# - ol; 3- methoxy - #<SP>1,3,5,(10),8</SP> - estratetraen - 17# - ol to the corresponding #<SP>2</SP>'<SP>5(10)</SP>-estradiene; dl-3- methoxy - 18 - methyl - #<SP>1,3,5,(10),8</SP> estratetraen- 17 - one to dl - 3 - methoxy - 18 - methyl- #<SP>2,5(10)</SP> - estradien - 17# - ol; 3 - methoxy- #<SP>1,3,5(10)</SP> - 19 . nor - pregnatrien - 17α - ol - 20- one 20-ethyleneketal to the corresponding #<SP>2,5(10)</SP> - 19 - nor - pregnadiene; 3 - methoxy- #<SP>1,3,5(10),9(11) </SP>- estratetraen - 17# - ol to the corresponding #<SP>2,5(10)</SP> - estradiene; and 3- methoxy - 17 - ethylenedioxy - #<SP>1,3,5(10)</SP> - estratriene to the corresponding #<SP>2</SP>'<SP>5(10)</SP>-estradiene. Also, 3 - methoxy - 17# - t - butoxy - #<SP>1,3,5(10),9(11)</SP>- estratetraene is reduced and the product is hydrolysed to 19-nor-testosterone.
GB31660/74A 1973-07-18 1974-07-17 Electrolytic reduction of aromatic steroids Expired GB1478679A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732337155 DE2337155A1 (en) 1973-07-18 1973-07-18 ELECTROLYTIC REDUCTION OF AROMATIC STEROIDS

Publications (1)

Publication Number Publication Date
GB1478679A true GB1478679A (en) 1977-07-06

Family

ID=5887618

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31660/74A Expired GB1478679A (en) 1973-07-18 1974-07-17 Electrolytic reduction of aromatic steroids

Country Status (10)

Country Link
JP (1) JPS5032158A (en)
CA (1) CA1055881A (en)
CH (1) CH601493A5 (en)
DD (1) DD112996A5 (en)
DE (1) DE2337155A1 (en)
DK (1) DK131434B (en)
FR (1) FR2237981B1 (en)
GB (1) GB1478679A (en)
HU (1) HU169278B (en)
NL (1) NL7409717A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2814500C3 (en) * 1978-03-31 1981-07-30 Schering Ag Berlin Und Bergkamen, 1000 Berlin Process for making? 5 (10) -7 unsaturated steroids

Also Published As

Publication number Publication date
HU169278B (en) 1976-10-28
CA1055881A (en) 1979-06-05
DK131434C (en) 1975-12-08
DK376874A (en) 1975-03-17
DD112996A5 (en) 1975-05-12
JPS5032158A (en) 1975-03-28
NL7409717A (en) 1975-01-21
DE2337155A1 (en) 1975-02-20
DK131434B (en) 1975-07-14
CH601493A5 (en) 1978-07-14
FR2237981B1 (en) 1977-07-01
FR2237981A1 (en) 1975-02-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee