GB850447A - Processes for the manufacture of steroid derivatives and new steroid derivatives - Google Patents

Processes for the manufacture of steroid derivatives and new steroid derivatives

Info

Publication number
GB850447A
GB850447A GB29470/58A GB2947058A GB850447A GB 850447 A GB850447 A GB 850447A GB 29470/58 A GB29470/58 A GB 29470/58A GB 2947058 A GB2947058 A GB 2947058A GB 850447 A GB850447 A GB 850447A
Authority
GB
United Kingdom
Prior art keywords
keto
compound
dione
trihalomethyl
group
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
GB29470/58A
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 GB850447A publication Critical patent/GB850447A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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 16a -trihalomethyl-20-keto compounds of the pregnane series and 16a -methyl-pregnan-3a -ol-11, 20-dione, and a process for the preparation of 16a -trihalomethyl-20-keto compounds of the pregnane series by subjecting a 16-dehydro-20-keto compound of the pregnane series to an addition reaction with haloform with the optional further step of hydrogenating the 16a -trihalomethyl compound in the presence of a dehalogenation catalyst such as Raney nickel, to form the corresponding 16a -methyl compound. The reactants used in the above process may contain substituents in other positions of the molecule such as free or functionally converted hydroxy groups, or double bonds. If a free 3-keto group is desired in the end product it must be protected during the reaction with haloform, e.g. by conversion to an ethylene ketal group, or a reactant may be used containing a 3-hydroxy group which may subsequently be oxidised to a 3-keto group. In the examples: (1) 16a -tribromomethyl-\se5-pregnenolone is prepared and is then hydrogenated to form 16a -methylpregnenolone and then oxidised to 16a -methylprogesterone; (2) 5 : 16-pregnadiene3b -ol-20-one in treated with chloroform to form the corresponding 16a -trichloromethyl compound and is then treated with t-butanol to form 16a -trichloromethyl-\se5-pregnene-3b -t-butoxy-20-one; (3) 16a -tribromomethyl-pregnon-3a -ol-11, 20 - dione is prepared and is hydrogenated to form 16a -methylpregnan-3a -ol-11, 20-dione.
GB29470/58A 1957-11-23 1958-09-15 Processes for the manufacture of steroid derivatives and new steroid derivatives Expired GB850447A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE850447X 1957-11-23

Publications (1)

Publication Number Publication Date
GB850447A true GB850447A (en) 1960-10-05

Family

ID=6777556

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29470/58A Expired GB850447A (en) 1957-11-23 1958-09-15 Processes for the manufacture of steroid derivatives and new steroid derivatives

Country Status (1)

Country Link
GB (1) GB850447A (en)

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