GB759705A - Cyclopentanophenanthrene derivatives and a method for the preparation thereof - Google Patents
Cyclopentanophenanthrene derivatives and a method for the preparation thereofInfo
- Publication number
- GB759705A GB759705A GB6162/53A GB616253A GB759705A GB 759705 A GB759705 A GB 759705A GB 6162/53 A GB6162/53 A GB 6162/53A GB 616253 A GB616253 A GB 616253A GB 759705 A GB759705 A GB 759705A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- dione
- pregnene
- refluxed
- dione acetate
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises D 1-allopregnene-, di4-pregnene- and D 1,4-pregnadiene-11a :17a -D ol-3:20-dione, their 11-esters, and processes for their preparation. The D 1-allopregnene-and D 1,4-pregnadiene compounds are prepared from allopregnane-11a :17a -diol-3:20-dione or an 11-ester thereof by selective bromination to yield the corresponding 2-bromo- and 2:4-dibromoderivatives, which are thereafter dehydrobrominated. The D 4 - pregnene compounds are obtained either (a) from allopregnane - 11a :17a - diol - 3:20 - dione or an 11-ester thereof, by polybrominating in at least the 2- and 4-positions of Ring A, treating the resultant bromo compound with sodium iodide in the presence of a lower aliphatic ketone to form the corresponding 2-iodo-D 4-pregnene, which is thereafter dehalogenated. In examples: (1) allopregnane-11a ,17a -diol-3,20-dione acetate is brominated in acetic acid containing HBr and the resulting 2-bromo derivative refluxed with 2,6-lutidine or collidine to yield D 1-allopregnene-11a ,17a -diol-3,20-dione acetate, which is saponified with alcoholic KOH to the free diol; (2) the 2-bromo derivative from (1) is dehydrobrominated by reaction with semicarbazide or 2,4-dinitrophenylhydrazine, treating the carbonyl derivative produced with pyruvic acid; (3) allopregnane-11a ,17a -diol-3,20-dione acetate is brominated as in (1), using 2 mols. bromine, to give the 2,4-dibromo derivative, which is refluxed with collidine giving D 1,f - pregnadiene - 11a ,17a - diol - 3,20 - dione acetate, subsequently saponified to the free diol; (4) the dibromo derivative from (3) is refluxed with NaI in acetone or methyl ethyl ketone, giving 2 - iodo - D 4 - pregnene - 11a ,17a - diol - 3,20-dione acetate, which is either refluxed with collidine (or lutidine or dimethylaniline), or treated with chromous chloride (or Raney nickel), yielding D 4-pregnene-11a ,17a -diol-3,20-dione acetate, subsequently saponified to the free diol; (5) 16a ,17a -oxido-allopregnan-11a -ol-3,20-dione acetate is brominated as in (3), giving 2,4,6 - tribromo - allopregnane - 11a ,17a -diol-3,20-dione acetate, which is refluxed with NaI in acetone and the resulting 2-iodo-16bromo - D 4 - pregnene - 11a ,17a - diol - 3,20-dione acetate refluxed with Raney nickel in ethanol to produce D 4-pregnene-11a ,17a -diol-3,20-dione acetate. Specifications 693,991 and 748,887 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MX759705X | 1952-03-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB759705A true GB759705A (en) | 1956-10-24 |
Family
ID=19743006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6162/53A Expired GB759705A (en) | 1952-03-07 | 1953-03-05 | Cyclopentanophenanthrene derivatives and a method for the preparation thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB759705A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2981659A (en) * | 1959-05-01 | 1961-04-25 | Upjohn Co | Method for the microbiological conversion of pregnane series steroids |
-
1953
- 1953-03-05 GB GB6162/53A patent/GB759705A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2981659A (en) * | 1959-05-01 | 1961-04-25 | Upjohn Co | Method for the microbiological conversion of pregnane series steroids |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB759705A (en) | Cyclopentanophenanthrene derivatives and a method for the preparation thereof | |
DE1468035A1 (en) | Process for the preparation of 19-alkyl steroids | |
US2734899A (en) | Manufacture of bromevated steroid | |
US2831872A (en) | Synthesis of steroids | |
US2846456A (en) | Steroid 21-aldehydes | |
US2531688A (en) | Preparation of esters of 7-halogeno-cholesterol | |
US3004966A (en) | 6-methyl steroid compounds and method for preparing same | |
US2666072A (en) | Halogenation and oxidation of steroids | |
US2876237A (en) | 5,7-pregnadiene-3-ol-20 one, esters thereof and related compounds | |
ES395740A1 (en) | Novel 6alpha,16alpha-dimethyl steroids | |
US2811537A (en) | delta-3, 11, 20-triketo-17-hydroxy-21-acyloxy-pregnadiene | |
GB772799A (en) | Cyclopentanophenanthrene derivatives and a method for the preparation thereof | |
GB823940A (en) | Steroid compounds | |
GB715402A (en) | 16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them | |
US2997487A (en) | Novel process for the preparation of a 16, 17-dehydro substituted pregnane and intermediates therefor | |
GB816909A (en) | Improvements in or relating to steroids | |
GB946659A (en) | 18-oxygenated steroids and process for their manufacture | |
GB512954A (en) | Manufacture of ketones or secondary alcohols of the cyclopentanopolyhydrophenanthrene series | |
GB826365A (en) | Steroid compounds | |
GB970482A (en) | New 17-desoxy corticosteroids and processes for their preparation | |
GB940344A (en) | Process for the manufacture of unsaturated steroids | |
GB826364A (en) | Cyclopentanopolyhydrophenanthrene compounds | |
GB464396A (en) | Process for the manufacture of androstenol-(17)-ones-(3) and derivatives thereof | |
GB787395A (en) | Substituted pregnanediones and process for their manufacture | |
GB944718A (en) | New steroid compounds and processes for their preparation |