ES255202A1 - Processes for the production of steroid compounds - Google Patents
Processes for the production of steroid compoundsInfo
- Publication number
- ES255202A1 ES255202A1 ES0255202A ES255202A ES255202A1 ES 255202 A1 ES255202 A1 ES 255202A1 ES 0255202 A ES0255202 A ES 0255202A ES 255202 A ES255202 A ES 255202A ES 255202 A1 ES255202 A1 ES 255202A1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- pregna
- trione
- groups
- protected
- 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
- 238000000034 method Methods 0.000 title abstract 2
- -1 steroid compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 238000001149 thermolysis Methods 0.000 abstract 2
- LGTKFVPODFIZBN-CAMGMKABSA-N (8S,9S,10S,13S,14S)-17-acetyl-10,13,16-trimethyl-2,4,5,6,7,8,9,12,14,15-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound CC1=C(C(C)=O)[C@]2(CC([C@@H]3[C@]4(CCC(CC4CC[C@H]3[C@@H]2C1)=O)C)=O)C LGTKFVPODFIZBN-CAMGMKABSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- 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
- 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 11a ,17a -dihydroxy-16a -methyl-pregna-3,20-dione, the 3,20-diketals thereof, and a process for the preparation of compounds of the formula: <FORM:0934703/IV(a)/1> wherein R is =H(a -OH) or = O, which comprises condensing pregn-16-en-3,11,20-trione with diazo-methane in an inert organic solvent to form the corresponding 16,17-pyrazoline, subjecting this compound to thermolysis to form 16-methyl-pregn-16-en-3,11,20-trione, protecting the 3- and 20-keto groups of this compound, epoxidising the resultant product to form the corresponding 16a ,17a -epoxy-16b -methyl-pregna-3, 11,20-trione derivative wherein the 3 and 20 groups are protected, reacting this derivative with an alkali metal or an alkaline earth metal in the presence of a lower aliphatic amine to break the epoxide bridge, invert the steric position of the 16-methyl group and reduce the 11-ketone function, thereby obtaining the 11a ,17a -dihydroxy-16a -methyl-pregna-3,20-dione derivative wherein the 3- and 20- groups are protected and thereafter reliberating the protected keto groups to yield the desired compound in which R is =H(a -OH) followed, if desired, by oxidation of the latter to give the desired compound in which R is =O. Thermolysis of the 16,17-pyrazoline is effected by heating in a high b.p. solvent. The breaking of the epoxide bridge may be effected with lithium in the presence of monomethylamine at 0 DEG C. to -40 DEG C. Specifications 807,203, 874,779, 934,701 and 934,712 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR784845A FR1234733A (en) | 1959-01-23 | 1959-01-23 | Process for preparing 16 alpha-methyl pregnane-diones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES255202A1 true ES255202A1 (en) | 1960-11-16 |
Family
ID=8710465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0255202A Expired ES255202A1 (en) | 1959-01-23 | 1960-01-22 | Processes for the production of steroid compounds |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE586857A (en) |
| CH (1) | CH369757A (en) |
| ES (1) | ES255202A1 (en) |
| FR (1) | FR1234733A (en) |
| GB (2) | GB934703A (en) |
-
1959
- 1959-01-23 FR FR784845A patent/FR1234733A/en not_active Expired
-
1960
- 1960-01-06 CH CH3860A patent/CH369757A/en unknown
- 1960-01-22 ES ES0255202A patent/ES255202A1/en not_active Expired
- 1960-01-22 BE BE586857A patent/BE586857A/en unknown
- 1960-01-22 GB GB243560A patent/GB934703A/en not_active Expired
- 1960-01-22 GB GB1645062A patent/GB934712A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB934703A (en) | 1963-08-21 |
| GB934712A (en) | 1963-08-21 |
| FR1234733A (en) | 1960-10-19 |
| CH369757A (en) | 1963-06-15 |
| BE586857A (en) | 1960-07-22 |
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