GB736182A - Halogenation of steroid compounds - Google Patents

Halogenation of steroid compounds

Info

Publication number
GB736182A
GB736182A GB19384/53A GB1938453A GB736182A GB 736182 A GB736182 A GB 736182A GB 19384/53 A GB19384/53 A GB 19384/53A GB 1938453 A GB1938453 A GB 1938453A GB 736182 A GB736182 A GB 736182A
Authority
GB
United Kingdom
Prior art keywords
chloro
hydroxy
trione
dione
dihydroxypregnane
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
GB19384/53A
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 GB736182A publication Critical patent/GB736182A/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

Abstract

A 4 - halo - 17(a ) - hydroxy - 3 - ketopregnene is obtained by reacting a 17(a )-hydroxy-3-ketopregnane with chlorine or bromine in the presence of an N,N-dialkylacylamide, e.g. an N,N-dialkylacylamide having the formula <FORM:0736182/IV (b)/1> wherein R1, R2 and R3 are lower alkyl radicals containing one to eight carbon atoms. The reaction may be effected between 0 DEG and 40 DEG C. in the presence of an acid catalyst, e.g. p-toluenesulphonic acid, naphthalene sulphonic acid or sulphuric acid. Examples disclose the production of 4-bromo- and 4-chloro-17(a )-hydroxy - 21 - acetoxy - pregnane - 3,11,20-trione. Other products which may be obtained are 4-bromo-17(a )-hydroxy-21-propionyloxy-, -butyryloxy, -benzoyloxy-, pentanoyloxy-, octanoyloxy-, hexanoyloxy-, heptanoyloxy-, or trimethylacetoxy-pregnane-3,11,20-trione, and the corresponding 4-chloro-derivatives, 4-chloro - 17(a ) - hydroxypregnane - 3,11,20-trione, 4-chloro-17(a )-hydroxypregnane-3,20-dione, 4-chloro-17(a ),21-dihydroxypregnane-3,11,20-trione, 4-chloro-17(a ), 11(a )-dihydroxypregnane - 3,20 - dione, 4 - chloro - 21 - acetoxy-17(a ), 11(b )-dihydroxypregnane-3,20-dione, 4-chloro - 17(a ) - hydroxy - 11(a ) - acetoxypregnane - 3,20 - dione, 4 - chloro - 17(a )-hydroxy - 20, 21 - diacetoxypregnane - 3 - one and the corresponding 4-bromo-compounds. Specification 710,557 is referred to.
GB19384/53A 1952-07-16 1953-07-13 Halogenation of steroid compounds Expired GB736182A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US736182XA 1952-07-16 1952-07-16

Publications (1)

Publication Number Publication Date
GB736182A true GB736182A (en) 1955-09-07

Family

ID=22114777

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19384/53A Expired GB736182A (en) 1952-07-16 1953-07-13 Halogenation of steroid compounds

Country Status (1)

Country Link
GB (1) GB736182A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3461117A (en) * 1957-07-22 1969-08-12 Schering Corp 3alpha,20 - diacetoxy - 16beta - lower alkyl - 17(20)-oxido- pregnane-11-one and intermediate in the preparation thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3461117A (en) * 1957-07-22 1969-08-12 Schering Corp 3alpha,20 - diacetoxy - 16beta - lower alkyl - 17(20)-oxido- pregnane-11-one and intermediate in the preparation thereof

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