GB1045474A - 8ª‰-methyl-11ª‰-hydroxysteroids and their preparation - Google Patents
8ª‰-methyl-11ª‰-hydroxysteroids and their preparationInfo
- Publication number
- GB1045474A GB1045474A GB3349063A GB3349063A GB1045474A GB 1045474 A GB1045474 A GB 1045474A GB 3349063 A GB3349063 A GB 3349063A GB 3349063 A GB3349063 A GB 3349063A GB 1045474 A GB1045474 A GB 1045474A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- steroid
- oxo
- methyl
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-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
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises (1) a process for preparing an 8b -methyl-11b -hydroxy-steroid by lactonizing an 8b -cyano-11b -hydroxy steroid by acid treatment, acylating the carboimidic acid lactone, subjecting the N-acylated lactone to reductive fission, hydrolysing the resulting 8b -iminomethyl-11b -hydroxy-steroid and reducing the resulting 8b -formyl-11b -hydroxysteroid; and (2) 8b -methyl-5a -22-ergostene-3b ,11b -diol and 3,3: 17,17-bisethylenedioxy-8b methyl-5-androsten-11b -ol. The starting material for process (1) may be of the androstane, pregnane, cholane, cholestane, sitostane, ergostane or spirostane series and may contain free or functionally converted hydroxyl and oxo groups and double bonds. The lactonization may be effected with an organic or inorganic acid or a Lewis acid; the acylation with an acid halide or anhydride derived from an alkanoic or aromatic carboxylic acid or alkyl or aryl carbonic acid; the reductive fission by the Birch reduction, which if effected in the presence of a proton source gives the 8-iminomethyl steroid directly or which if effected on an N-alkoxycarbonyl compound in the absence of a proton source gives an N-alkoxycarbonyl dihydro carboimidic acid lactone which is then hydrolysed with an alkali to the required 8-iminomethyl compound; the hydrolysis of the last-named compound by an acid, salt or metal oxide; and the reduction by the WolffKisler method or Huang-Minlon modification thereof. Examples are given. 8b -Cyano-11b -hydroxy-stroids are prepared by treating 9a -halogeno-11-oxo-steroids with a basic agent to give D 8(9)-11-oxo-steroids, treating these with hydrocyanic acid and a trialkyl aluminium to give 8b -cyano-11-oxo-steroids, and reducing these. 3,3:17,17-bisethylenedioxy-11 -keto-5,8-androstadiene, used in this process, is prepared by ketalization of the 3,11,17-trione. 9a - Bromo - 3,11,17 - triketo - 4 - androstene is prepared by oxidation of the 11b -ol.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3653162 | 1962-08-24 | ||
JP3653362 | 1962-08-24 | ||
JP3653462 | 1962-08-24 | ||
JP3653262 | 1962-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1045474A true GB1045474A (en) | 1966-10-12 |
Family
ID=27460278
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB597665A Expired GB1045476A (en) | 1962-08-24 | 1963-08-23 | 8ª‰-substituted-11ª‰-hydroxysteroids and their preparation |
GB3349063A Expired GB1045474A (en) | 1962-08-24 | 1963-08-23 | 8ª‰-methyl-11ª‰-hydroxysteroids and their preparation |
GB597565A Expired GB1045475A (en) | 1962-08-24 | 1963-08-28 | Steroid 8ª‰,11ª‰-carboimidic lactones and their preparation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB597665A Expired GB1045476A (en) | 1962-08-24 | 1963-08-23 | 8ª‰-substituted-11ª‰-hydroxysteroids and their preparation |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB597565A Expired GB1045475A (en) | 1962-08-24 | 1963-08-28 | Steroid 8ª‰,11ª‰-carboimidic lactones and their preparation |
Country Status (2)
Country | Link |
---|---|
CH (1) | CH441298A (en) |
GB (3) | GB1045476A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109180775B (en) * | 2018-09-05 | 2021-03-23 | 常州大学怀德学院 | C-28 imine substituted betulin isomer derivative and preparation method and application thereof |
-
1963
- 1963-08-19 CH CH1021163A patent/CH441298A/en unknown
- 1963-08-23 GB GB597665A patent/GB1045476A/en not_active Expired
- 1963-08-23 GB GB3349063A patent/GB1045474A/en not_active Expired
- 1963-08-28 GB GB597565A patent/GB1045475A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB1045476A (en) | 1966-10-12 |
GB1045475A (en) | 1966-10-12 |
CH441298A (en) | 1967-08-15 |
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