GB957221A - Novel steroid compounds and processes for their preparation - Google Patents
Novel steroid compounds and processes for their preparationInfo
- Publication number
- GB957221A GB957221A GB4668863A GB4668863A GB957221A GB 957221 A GB957221 A GB 957221A GB 4668863 A GB4668863 A GB 4668863A GB 4668863 A GB4668863 A GB 4668863A GB 957221 A GB957221 A GB 957221A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epoxy
- methyl
- processes
- preparation
- hydroxy
- 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 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
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
- 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 18, 20b -epoxy-11b -hydroxy-16a -methyl-15b -pregnane compounds of the formula: <FORM:0957221/C2/1> in which R1 is either a hydroxy group in the a -orientation or the oxygen atom of a keto group and processes for the preparation thereof wherein 3a -acyloxy-18, 20b -epoxy-16a -methyl-5b -pregnan-11-one of the formula: <FORM:0957221/C2/2> (wherein Ac represents the acyl radical derived from an organic carboxylic acid) is subjected to simultaneous reduction and saponification by an alkaline reducing agent to yield 3a , 11b -dihydroxy-18, 20b -epoxy-16a -methyl-5b -pregnane and further subjected to selective oxidation to yield 11b -hydroxy-18, 20b -epoxy-16a -methyl-5b -pregnan-3-one. As alkaline reducing agent there may be used potassium borohydride. Oxidation may be effected with aluminium isopropylate in toluene and cyclohexanone. Specification 903,808 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR834359A FR1365260A (en) | 1960-07-29 | 1960-07-29 | New oxygenated steroid derivatives and method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB957221A true GB957221A (en) | 1964-05-06 |
Family
ID=8736474
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4668863A Expired GB957221A (en) | 1960-07-29 | 1961-07-26 | Novel steroid compounds and processes for their preparation |
| GB4668763A Expired GB957220A (en) | 1960-07-29 | 1961-07-26 | A novel steroid compound and processes for its preparation |
| GB2705561A Expired GB957219A (en) | 1960-07-29 | 1961-07-26 | New steroid compounds and processes for their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4668763A Expired GB957220A (en) | 1960-07-29 | 1961-07-26 | A novel steroid compound and processes for its preparation |
| GB2705561A Expired GB957219A (en) | 1960-07-29 | 1961-07-26 | New steroid compounds and processes for their preparation |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH400145A (en) |
| FR (1) | FR1365260A (en) |
| GB (3) | GB957221A (en) |
-
1960
- 1960-07-29 FR FR834359A patent/FR1365260A/en not_active Expired
-
1961
- 1961-07-11 CH CH808761A patent/CH400145A/en unknown
- 1961-07-26 GB GB4668863A patent/GB957221A/en not_active Expired
- 1961-07-26 GB GB4668763A patent/GB957220A/en not_active Expired
- 1961-07-26 GB GB2705561A patent/GB957219A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB957219A (en) | 1964-05-06 |
| CH400145A (en) | 1965-10-15 |
| GB957220A (en) | 1964-05-06 |
| FR1365260A (en) | 1964-07-03 |
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