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GB907190A - 21-trihalo steroids and a process for the manufacture thereof - Google Patents

21-trihalo steroids and a process for the manufacture thereof

Info

Publication number
GB907190A
GB907190A GB1538159A GB1538159A GB907190A GB 907190 A GB907190 A GB 907190A GB 1538159 A GB1538159 A GB 1538159A GB 1538159 A GB1538159 A GB 1538159A GB 907190 A GB907190 A GB 907190A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
acetic acid
trichloro
trihalogeno
compound
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
GB1538159A
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 GB907190A publication Critical patent/GB907190A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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

The invention comprises a 21 : 21 : 21-trihalogeno-20-hydroxy-steroidparticularly the trichloro compound, and the preparation thereof by bringing together a 17-formyl-steroid, which may contain one or more inert substituents, and haloform with an alkali metal alcoholate such as potassium tertiary butylate-preferably at a low temperature. The 17-formyl-steroid reactant may contain a carbon-carbon double bond or as an inert substituent a hydroxyl or keto group in a free or functionally converted form. The process is preferably carried out in an inert organic solvent such as a mixture of t-butanol and tetrahydrofuran. The above process may be amplified in that the 21 : 21 : 21-trihalogeno-20-hydroxy-steroid may be oxidised e.g. to oxidise a 3-hydroxy group to a 3-keto group or to form a 21 : 21 : 21-trihalogeno-20-keto-steroid. A suitable oxidising agent is bichromate in glacial acetic acid. In addition, the 21 : 21 : 21-trihalogeno-20-hydroxy- and the 21 : 21 : 21-trihalogeno-20-keto-steroids may be subjected to hydrolysis to form a 17b -yl-hydroxy-acetic acid, and the carboxylic group thereof may then be converted into a functional derivative thereof e.g. by esterification or amidation or by reaction with a Grignard reagent or a similar reagent such as a lithium alkyl or zinc alkyl to increase the length of the side chain. In Examples: (1) 17b -formyl-testan-3a -ol is reacted with chloroform to form 21 : 21 : 21-trichloro-pregnane-3a -20#x-diol, this compound is either oxidised with aluminum isopropylate and cyclohexanone to form 21 : 21 : 21-trichloro-20#x-hydroxy-pregnan-3-one or hydrolysed with sodium hydroxide to form 3a -hydroxy-5b -androstane-17b -yl-hydroxy acetic acid, the latter compound may then be acetylated to form 3a -acetoxy-5b -androstane-17b -yl-hydroxy-acetic acid, converted to the corresponding acid chloride by reaction with oxalyl chloride, the acid chloride is then reacted with morpholine to form N-(3a -acetoxy-5b -androstane-17b -yl-hydroxy acetic acid)-morpholine which is finally hydrolysed to the corresponding 3a -hydroxy compound; and (2) 17b -formyl-D 4-androsten-3b -ol is reacted with chloroform to form 21 : 21 : 21-trichloro-D 4-pregnene-3b :20#x-diol this compound is either oxidised as in (1) to form 21 : 21 : 21-trichloro-D 4-pregnen-20#x-ol-3-one and then further oxidised with sodium bichromate to form 21 : 21 : 21-trichloro-D 4-pregnene-3,20-dione or is hydrolysed as in (1) to form D 4-androstene-17b -yl-hydroxy-acetic acid-3-one which is then reacted with b -diethylaminoethyl chloride to form the b -diethylaminoethyl ester of D 4-androstene-17b -yl-hydroxy-acetic acid-3-one.
GB1538159A 1958-05-23 1959-05-05 21-trihalo steroids and a process for the manufacture thereof Expired GB907190A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESC024121 1958-05-23

Publications (1)

Publication Number Publication Date
GB907190A true GB907190A (en) 1962-10-03

Family

ID=7429806

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1538159A Expired GB907190A (en) 1958-05-23 1959-05-05 21-trihalo steroids and a process for the manufacture thereof

Country Status (3)

Country Link
BE (1) BE578164A (en)
CH (1) CH376497A (en)
GB (1) GB907190A (en)

Also Published As

Publication number Publication date
CH376497A (en) 1964-04-15
BE578164A (en) 1959-08-17

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