GB1139812A - Oxidation of steroids - Google Patents

Oxidation of steroids

Info

Publication number
GB1139812A
GB1139812A GB3819966A GB3819966A GB1139812A GB 1139812 A GB1139812 A GB 1139812A GB 3819966 A GB3819966 A GB 3819966A GB 3819966 A GB3819966 A GB 3819966A GB 1139812 A GB1139812 A GB 1139812A
Authority
GB
United Kingdom
Prior art keywords
compounds
prepared
steroids
keto
hydroxy
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
GB3819966A
Inventor
Bjarte Loeken
Irving V Sollins
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.)
Phytogen Products Inc
Original Assignee
Phytogen Products Inc
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 Phytogen Products Inc filed Critical Phytogen Products Inc
Priority to GB3819966A priority Critical patent/GB1139812A/en
Publication of GB1139812A publication Critical patent/GB1139812A/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
    • 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

1,139,812. Oxidation of steroids. PHYTOGEN PRODUCTS Inc. 25 Aug., 1966, No. 38199/66. Heading C2U. The invention comprises (a) a process for converting 3-hydroxy-#5-androatenes or pregnenes to the corresponding 3-keto-#5-steroids by oxidation in acetone, tetrahydrofuran or butanone solution with chromium trioxide and sulphuric acid at 0-25‹ C. for a period not exceeding 6 minutes, and quenching the reaction, with optional isomerization in situ to the corresponding 3-keto-#4-steroids, and (b) compounds of formula where X is hydrogen or fluorine and R is hydrogen or C 1-8 acyl. The compounds of the invention have progestational activity. 3-Ethylene ketals and thioketals of the compounds of the invention are prepared by standard ketalizations. 17α - Hydroxy - 16# - bromo - pregn - 4 - en- 3,20-dione and its 21-acetoxy analogue are prepared by reaction of the corresponding 16α,17α- oxido-3-keto-#5 compounds with hydrogen bromide. 17α - Hydroxy - 21 - acetoxy - pregn - 4 - en- 3,20-dione is prepared by refluxing the corresponding 16#-bromo compound in methanol with Raney nickel. 17α - Hexanoyloxy - 6 - methyl - pregnenolone is prepared by acylation of 6-methyl-pregnenolone acetate, followed by partial hydrolysis to the 3-ol.
GB3819966A 1966-08-25 1966-08-25 Oxidation of steroids Expired GB1139812A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3819966A GB1139812A (en) 1966-08-25 1966-08-25 Oxidation of steroids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3819966A GB1139812A (en) 1966-08-25 1966-08-25 Oxidation of steroids

Publications (1)

Publication Number Publication Date
GB1139812A true GB1139812A (en) 1969-01-15

Family

ID=10401902

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3819966A Expired GB1139812A (en) 1966-08-25 1966-08-25 Oxidation of steroids

Country Status (1)

Country Link
GB (1) GB1139812A (en)

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