GB887706A - Improvements in the conversion of steroidal ª-:ª- unsaturated ketones to olefines - Google Patents
Improvements in the conversion of steroidal ª-:ª- unsaturated ketones to olefinesInfo
- Publication number
- GB887706A GB887706A GB1907557A GB1907557A GB887706A GB 887706 A GB887706 A GB 887706A GB 1907557 A GB1907557 A GB 1907557A GB 1907557 A GB1907557 A GB 1907557A GB 887706 A GB887706 A GB 887706A
- Authority
- GB
- United Kingdom
- Prior art keywords
- unsaturated
- ene
- androst
- grouping
- weight
- 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
- 238000006243 chemical reaction Methods 0.000 title 1
- 150000002576 ketones Chemical class 0.000 title 1
- 230000003637 steroidlike Effects 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- 150000003431 steroids Chemical class 0.000 abstract 3
- 229960000583 acetic acid Drugs 0.000 abstract 2
- -1 glacial acetic acid Chemical compound 0.000 abstract 2
- RJWNCDOWHNLVPF-HQEMIIEJSA-N (8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1=CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 RJWNCDOWHNLVPF-HQEMIIEJSA-N 0.000 abstract 1
- TTXJJFWWNDJDNR-CZRUWHASSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-one Chemical compound C1CC=CC2=CC(=O)[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]3[C@]21C TTXJJFWWNDJDNR-CZRUWHASSA-N 0.000 abstract 1
- SFBMPHLOQAKIBY-LDHZKLTISA-N (8s,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 SFBMPHLOQAKIBY-LDHZKLTISA-N 0.000 abstract 1
- TTXJJFWWNDJDNR-UHFFFAOYSA-N 3,5-cholestadien-7-one Natural products C1CC=CC2=CC(=O)C3C4CCC(C(C)CCCC(C)C)C4(C)CCC3C21C TTXJJFWWNDJDNR-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- OYEYIKXHJYRVQH-AQHAWAMTSA-N [(3s,8s,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1=CC2C[C@@H](OC(C)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 OYEYIKXHJYRVQH-AQHAWAMTSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- 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 21-acetoxy-17a -hydroxy-5a (and 5-b )-pregn-3-ene-11,20-dione, 17b -acetoxy-5a - (and -5b )-androst-3-ene and 11b -hydroxy-5-androst-3-en-17-one, and a process for reducing by means of zinc and acetic acid, e.g. glacial acetic acid, 4,5-unsaturated-3-oxo and 5,6-unsaturated-7-oxo steroids containing the grouping <FORM:0887706/IV (b)/1> and free from substituents which sterically hinder the keto group from reacting to convert the above grouping into a grouping of the formula <FORM:0887706/IV (b)/2> and so produce respectively 3,4-unsaturated or a 6,7-unsaturated steroids, the weight of zinz employed is at least 10 times the weight of the steroid, e.g. at least 1,000 times the weight of the steroid. In the examples the compounds detailed above and cholest-3-ene, 3b -acetoxycholest - 6 - ene, cholesta - 3, 5 - dien - 7 - one, and androst-3-en-17-one are prepared.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1907557A GB887706A (en) | 1957-06-17 | 1957-06-17 | Improvements in the conversion of steroidal ª-:ª- unsaturated ketones to olefines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1907557A GB887706A (en) | 1957-06-17 | 1957-06-17 | Improvements in the conversion of steroidal ª-:ª- unsaturated ketones to olefines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB887706A true GB887706A (en) | 1962-01-24 |
Family
ID=10123356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1907557A Expired GB887706A (en) | 1957-06-17 | 1957-06-17 | Improvements in the conversion of steroidal ª-:ª- unsaturated ketones to olefines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB887706A (en) |
-
1957
- 1957-06-17 GB GB1907557A patent/GB887706A/en not_active Expired
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