GB1557757A - Process for preparing 16 methyl steroids - Google Patents

Process for preparing 16 methyl steroids

Info

Publication number
GB1557757A
GB1557757A GB1077878A GB1077878A GB1557757A GB 1557757 A GB1557757 A GB 1557757A GB 1077878 A GB1077878 A GB 1077878A GB 1077878 A GB1077878 A GB 1077878A GB 1557757 A GB1557757 A GB 1557757A
Authority
GB
United Kingdom
Prior art keywords
alpha
acetoxypregna
dioxo
fluoro
beta
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
GB1077878A
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 GB1557757A publication Critical patent/GB1557757A/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
    • C07J5/0007—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 not substituted in position 17 alfa
    • C07J5/0023—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 not substituted in position 17 alfa substituted in position 16
    • C07J5/003—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes
    • C07J5/0038—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes by an alkyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

To prepare 3,20-dioxo-9 alpha -fluoro-11 beta -hydroxy-16 alpha -methyl-21-acetoxypregna-1,4-diene , a methylmagnesium halide is reacted with 3,20-dioxo-9 alpha -fluoro-11 beta -hydroxy-21-acetoxypregna-1,4,16-triene in the presence of a catalytic quantity of a cuprous halide, the magnesium compound protonated, the resultant crude product acetylated by the action of an acetylating agent, the reacetylated crude product purified using an organic solvent, the product treated in solution using a peroxidising agent and again purified using an organic solvent. The compound obtained is an intermediate in the synthesis of dexamethasone 21-acetate.
GB1077878A 1977-03-18 1978-03-17 Process for preparing 16 methyl steroids Expired GB1557757A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7708170A FR2383968A1 (en) 1977-03-18 1977-03-18 PROCESS FOR THE PREPARATION OF A 16A-METHYL STEROIDE

Publications (1)

Publication Number Publication Date
GB1557757A true GB1557757A (en) 1979-12-12

Family

ID=9188293

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1077878A Expired GB1557757A (en) 1977-03-18 1978-03-17 Process for preparing 16 methyl steroids

Country Status (11)

Country Link
JP (1) JPS53116362A (en)
BE (1) BE865043A (en)
CA (1) CA1117936A (en)
CH (1) CH629223A5 (en)
DE (1) DE2811540A1 (en)
FR (1) FR2383968A1 (en)
GB (1) GB1557757A (en)
HU (1) HU174829B (en)
IE (1) IE46586B1 (en)
NL (1) NL7802927A (en)
PT (1) PT67790A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2735501A1 (en) * 1995-06-15 1996-12-20 Payen & Cie L Stretch cladded thick yarn prodn. covered with false twisted elements

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2244530B1 (en) * 1973-07-27 1977-07-01 Roussel Uclaf

Also Published As

Publication number Publication date
CH629223A5 (en) 1982-04-15
DE2811540A1 (en) 1978-09-21
IE780553L (en) 1978-09-18
FR2383968B1 (en) 1980-11-28
NL7802927A (en) 1978-09-20
JPS6123799B2 (en) 1986-06-07
HU174829B (en) 1980-03-28
BE865043A (en) 1978-09-18
FR2383968A1 (en) 1978-10-13
CA1117936A (en) 1982-02-09
IE46586B1 (en) 1983-07-27
PT67790A (en) 1978-04-01
JPS53116362A (en) 1978-10-11
DE2811540C2 (en) 1987-09-10

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940317