GB768271A - 4, 16-pregnadiene-3, 11, 20-trione and the production thereof - Google Patents

4, 16-pregnadiene-3, 11, 20-trione and the production thereof

Info

Publication number
GB768271A
GB768271A GB24874/54A GB2487454A GB768271A GB 768271 A GB768271 A GB 768271A GB 24874/54 A GB24874/54 A GB 24874/54A GB 2487454 A GB2487454 A GB 2487454A GB 768271 A GB768271 A GB 768271A
Authority
GB
United Kingdom
Prior art keywords
dione
pregnadiene
ketone
acyloxy group
sulphonyloxy
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
GB24874/54A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB768271A publication Critical patent/GB768271A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 4 : 16-pregnadiene-3 : 11 : 20-trione, and the preparation thereof by reacting a 4 : 17a -dihalo-11a -acyloxypregnane-3 : 20-dione with an organic hydrazine to form the 3-hydrazone of an 11a -acyloxy-17a -halo-4-pregnene-3 : 20-dione, converting this to the corresponding ketone, dehydrohalogenating this and hydrolysing the 11a -acyloxy group, and then oxidizing the resulting 11a -hydroxy-4 : 16-pregnadiene-3 : 20-dione. The steps preceding the final oxidation are carried out in accordance with Specification 768,269, except that the conversion of the hydrazone is not limited to an exchange reaction with a ketone or aldehyde whilst the acyloxy group may be any carboxylic acyloxy group or a sulphonyloxy or phosphonyloxy group. The oxidation may be effected by the Oppenauer method with an aluminium alcoholate and a ketone, by the action of chromic acid in a heterogeneous or homogeneous medium, or especially by means of a pyridinechromic anhydride complex, advantageously at 0-50 DEG C. In examples: (1) 11a -acetoxy-4 : 16-pregnadiene-3 : 20-dione is prepared as described in Example 1 of Specification 768,269 and oxidized with a slurry of chromic anhydride and pyridine at 20-25 DEG C.; (2) 11a -benzoyloxy-4 : 16-pregnadiene-3 : 20-dione is prepared as described in Example 5 of Specification 768,269 and oxidized with a solution of sodium dichromate in aqueous sulphuric acid. Lists are given of additional intermediates, including compounds in which the 11a -substituent is benzene-, p-toluene-, p-chlorobenzene- or a -naphthalene - sulphonyloxy or benzenephosphonyloxy. Specification 668,533 also is referred to.
GB24874/54A 1953-08-27 1954-08-26 4, 16-pregnadiene-3, 11, 20-trione and the production thereof Expired GB768271A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US768271XA 1953-08-27 1953-08-27

Publications (1)

Publication Number Publication Date
GB768271A true GB768271A (en) 1957-02-13

Family

ID=22134417

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24874/54A Expired GB768271A (en) 1953-08-27 1954-08-26 4, 16-pregnadiene-3, 11, 20-trione and the production thereof

Country Status (1)

Country Link
GB (1) GB768271A (en)

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