GB850447A - Processes for the manufacture of steroid derivatives and new steroid derivatives - Google Patents
Processes for the manufacture of steroid derivatives and new steroid derivativesInfo
- 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
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)
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.
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) |
-
1958
- 1958-09-15 GB GB29470/58A patent/GB850447A/en not_active Expired
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