GB737957A - Steroid ketals - Google Patents
Steroid ketalsInfo
- Publication number
- GB737957A GB737957A GB21285/53A GB2128553A GB737957A GB 737957 A GB737957 A GB 737957A GB 21285/53 A GB21285/53 A GB 21285/53A GB 2128553 A GB2128553 A GB 2128553A GB 737957 A GB737957 A GB 737957A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diketal
- dione
- diol
- chloro
- acid
- 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
- 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
- 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 3,20-cyclic diketal of a 4-chloro- or 4-bromo-pregnane-3,20-dione and the preparation thereof by mixing together an alkane-1,2-diol or an alkane-1,3-diol and a steroid 4-halo-3,20-dione having a pregnane carbon skeleton in the presence of an acid catalyst, e.g. m- and p-toluene sulphonic acids, naphthalene sulphonic acid, benzenesulphonic acid, ortho-chlorobenzenesulphonic acid, hydrochloric acid and sulphuric acid, at a temperature between about 20 DEG and 200 DEG C., to cause conversion of the 3- and 20-ketone groups to ketal groups. Examples disclose the production of 4 - chloro - 17a - hydroxypregnane - 3,11,20-trione 3,20-ethylene glycol diketal, 4-chloro-11b , 17a - dihydroxypregnane - 3,20 - dione 3,20-ethylene glycol diketal, 4-chloropregnane-3,20-dione 3,20-ethylene glycol diketal, 4-chloro-17a -hydroxypregnane-3,11,20-trione 3,20-propane-1,2 and 1,3-diol diketal, 4-bromo-17a -hydroxypregnane-3,11,20-trione 3,20-propane-1,2-diol diketal, 4 - bromo - 11b ,17a - dihydroxypregnane - 3,20 - dione - 3,20 - propane - 1,2 - diol diketal, 4 - bromopregnane - 3,11,20 - trione 3,20 - (3 - methyl - pentane - 1,2 - diol) - diketal, 4 - bromo - 12 - hydroxypregnane - 3,20 - dione 3,20 - propane - 1,3 - diol diketal and 4-chloro-11a ,17a - dihydroxypregnane - 3,20 - dione 3,20-ethylene glycol diketal.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US737957XA | 1952-08-16 | 1952-08-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB737957A true GB737957A (en) | 1955-10-05 |
Family
ID=22115847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21285/53A Expired GB737957A (en) | 1952-08-16 | 1953-07-31 | Steroid ketals |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB737957A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3052696A (en) * | 1960-03-16 | 1962-09-04 | Roussel Uclaf | Novel 16alpha-methyl-delta4, 9(11)-pregnadienes and preparation thereof |
US3079382A (en) * | 1958-04-16 | 1963-02-26 | Farmaceutici Italia | Process for the synthesis of 4-methyl-17-alpha-hydroxyprogesterone and its esters |
US3088945A (en) * | 1958-08-07 | 1963-05-07 | Merck & Co Inc | Process for the preparation of 12alpha-alkyl steroids |
-
1953
- 1953-07-31 GB GB21285/53A patent/GB737957A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3079382A (en) * | 1958-04-16 | 1963-02-26 | Farmaceutici Italia | Process for the synthesis of 4-methyl-17-alpha-hydroxyprogesterone and its esters |
US3088945A (en) * | 1958-08-07 | 1963-05-07 | Merck & Co Inc | Process for the preparation of 12alpha-alkyl steroids |
US3052696A (en) * | 1960-03-16 | 1962-09-04 | Roussel Uclaf | Novel 16alpha-methyl-delta4, 9(11)-pregnadienes and preparation thereof |
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