GB792224A - Synthesis of steroids - Google Patents

Synthesis of steroids

Info

Publication number
GB792224A
GB792224A GB30532/54A GB3053254A GB792224A GB 792224 A GB792224 A GB 792224A GB 30532/54 A GB30532/54 A GB 30532/54A GB 3053254 A GB3053254 A GB 3053254A GB 792224 A GB792224 A GB 792224A
Authority
GB
United Kingdom
Prior art keywords
fluoro
keto
bromo
hydroxyprogesterone
substituent
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
GB30532/54A
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.)
Olin Corp
Original Assignee
Olin Corp
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 Olin Corp filed Critical Olin Corp
Publication of GB792224A publication Critical patent/GB792224A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises a steroid of the pregnane series having a 3-keto or 3-hydroxy substituent, a 9a -fluoro substituent, an 11-keto or 11b -hydroxy substituent and a 20-keto substituent and preferably having the formula <FORM:0792224/IV (b)/1> wherein the 4,5-position is double-bonded or saturated, and R is -H, R1 is -OH, or together R and R1 is = O or a group convertible thereto by hydrolysis, R11 is -H, R111 is (b )-OH or together R11 and R111 is =O, Y is H, -OH, or -O-(acyl, and Z is either -H or (a )-OH and a process of preparing a steroid of the pregnane series having a 9a -fluoro substituent and an 11-keto or 11b -hydroxy substituent which comprises reacting a 9b ,11b -oxido steroid of the pregnane series with an agent furnishing hydrogen fluoride, and, if desired, oxidizing the 9a -fluoro-11b -hydroxy steroid thus formed to form the corresponding 9a -fluoro-11-keto derivative. The hydrofluorination may be effected in an alcohol-free solvent. Examples describe the production of 9a -fluorocorticosterone, 9a -fluoro-11-dehydrocorticosterone and the acetates thereof, 9a -fluoro-11b -hydroxyprogesterone, 9a - fluoro - 11 - keto - progesterone, 9a - fluoro - 11b ,17a - dihydroxyprogesterone and 9a -fluoro-11-keto-17a -hydroxyprogesterone. Starting compounds. 9b ,11b -oxido steroids of the pregnane series are obtained by dehydrobrominating the corresponding 9a -bromo-11b -hydroxy steroids, e.g. 9a -bromo- D 4-pregnene-11b ,17a ,21 - triol - 3,20 - dione, 9a - bromocorticosterone, 9a - bromo - 11b - hydroxyprogesterone, and 9a - bromo - 11b ,17a - dihydroxyprogesterone. 9a -Bromo-11b -hydroxyprogesterone is obtained by treating D 4,9(11)-pregnadiene-3,20-dione with N-bromacetamide in aqueous perchloric acid. 9a -Bromo-11b ,17a -dihydroxy progesterone is obtained in a similar manner. D 4,9(11)- Pregnadiene - 17a - ol - 3,20 - dione is obtained by treating 11-tosyloxy-17a -hydroxyprogesterone with anhydrous sodium acetate.
GB30532/54A 1954-03-10 1954-10-22 Synthesis of steroids Expired GB792224A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US792224XA 1954-03-10 1954-03-10

Publications (1)

Publication Number Publication Date
GB792224A true GB792224A (en) 1958-03-19

Family

ID=22149181

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30532/54A Expired GB792224A (en) 1954-03-10 1954-10-22 Synthesis of steroids

Country Status (1)

Country Link
GB (1) GB792224A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110698528A (en) * 2019-11-19 2020-01-17 湖南新合新生物医药有限公司 Methylprednisolone intermediate debrominated substance and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110698528A (en) * 2019-11-19 2020-01-17 湖南新合新生物医药有限公司 Methylprednisolone intermediate debrominated substance and preparation method thereof
CN110698528B (en) * 2019-11-19 2022-08-26 湖南新合新生物医药有限公司 Methylprednisolone intermediate debrominated substance and preparation method thereof

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