CH228433A - Process for the preparation of 2,4-dibromo-androstanol acetate- (17) -one- (3). - Google Patents
Process for the preparation of 2,4-dibromo-androstanol acetate- (17) -one- (3).Info
- Publication number
- CH228433A CH228433A CH228433DA CH228433A CH 228433 A CH228433 A CH 228433A CH 228433D A CH228433D A CH 228433DA CH 228433 A CH228433 A CH 228433A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dibromo
- acetate
- preparation
- androstanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- VFEWURLNQZFEPK-QANZEPGUSA-N C[C@](CCC1)(CC2)[C@@H]1[C@H](CC1)[C@H]2[C@@](C)(CC(C2)Br)[C@@H]1C2(O)Br Chemical compound C[C@](CCC1)(CC2)[C@@H]1[C@H](CC1)[C@H]2[C@@](C)(CC(C2)Br)[C@@H]1C2(O)Br VFEWURLNQZFEPK-QANZEPGUSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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)
Description
Verfahren zur Herstellung von 2,4-Dibrom-androstanolaeetat-(17)-on-(3).
EMI0001.0003
Gegenistand <SEP> des <SEP> vorliegenden <SEP> Patentes <SEP> ist
<tb> ein <SEP> Verfahren, <SEP> zur <SEP> Herstellung <SEP> von <SEP> 2,4-Di brom-aadrostanola;cet9,t-(17)-on-(3), <SEP> das <SEP> da durch <SEP> gekennzeichnet <SEP> isst, <SEP> dass <SEP> man <SEP> Andro stan.on-(3)-ol-a.cetat-(17) <SEP> mit <SEP> einem <SEP> bromie ren@den <SEP> Mittel <SEP> behandelt.
<tb>
Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> als <SEP> Arznei mittel <SEP> sowie <SEP> ale <SEP> Zwischenpmodukt <SEP> für <SEP> die
<tb> Herstellung <SEP> von <SEP> Arzneimitteln <SEP> Verwendung
<tb> finden.
<tb>
<I>Beispiel:</I>
<tb> 14 <SEP> g <SEP> Xndlrostanorn(3)-o@l-acetat-(17) <SEP> vom
<tb> Smp. <SEP> 157 <SEP> werden <SEP> in <SEP> 10 <SEP> cm@ <SEP> Eisessig <SEP> gelöst
<tb> und <SEP> bei <SEP> Zimmertemperatur <SEP> nach <SEP> Zusatz <SEP> von
<tb> einigen <SEP> Tropfen <SEP> Bromwasserstoff-Eisessig
<tb> im <SEP> Lauf <SEP> einer <SEP> halben <SEP> Stunde <SEP> mit <SEP> einer <SEP> Lö sung, <SEP> von <SEP> 4,28 <SEP> em# <SEP> Brom <SEP> in <SEP> 250,em' <SEP> Eisiessig
<tb> unter <SEP> Rühren <SEP> vernsetzt. <SEP> Die <SEP> entfärbte <SEP> Lösung
<tb> wird <SEP> vorsichtig <SEP> mit <SEP> Wasser <SEP> angespritzt, <SEP> wobei
<tb> das <SEP> rohe <SEP> 2,4-Dibrom-androstanoliacetat-(17)-
EMI0001.0004
on;
-(3) <SEP> ausflockt <SEP> und <SEP> sich <SEP> zusammenballt.
<tb> Nach <SEP> einigem <SEP> Stehen <SEP> filtriert <SEP> man <SEP> dass <SEP> Roh produkt <SEP> ab <SEP> und <SEP> kristaEisiert <SEP> es <SEP> aus <SEP> Alkohol
<tb> um. <SEP> Das <SEP> reine <SEP> .2,4-Dibmom.-ankostanoliac:etat (17)-on-(3,) <SEP> kristallisiert <SEP> aus <SEP> Alkohol <SEP> in <SEP> farb losen <SEP> Nadeln, <SEP> die <SEP> bei <SEP> 194 <SEP> unter <SEP> Zersetzung
<tb> schmelzen. <SEP> Ausbeute <SEP> 11,4 <SEP> g.
Process for the preparation of 2,4-dibromo-androstanolaeetat- (17) -one- (3).
EMI0001.0003
The object <SEP> of the <SEP> present <SEP> patent is <SEP>
<tb> a <SEP> process, <SEP> for the <SEP> production <SEP> of <SEP> 2,4-di bromo-aadrostanola; cet9, t- (17) -on- (3), <SEP> the <SEP> because marked by <SEP> <SEP> eats, <SEP> that <SEP> man <SEP> Andro stan.on- (3) -ol-a.cetat- (17) <SEP> with <SEP > a <SEP> brominate @ the <SEP> agent <SEP> treated.
<tb>
The <SEP> new <SEP> connection <SEP> should <SEP> as <SEP> medicament <SEP> as well as <SEP> as <SEP> intermediate product <SEP> for <SEP> the
<tb> Manufacture <SEP> of <SEP> drugs <SEP> use
<tb> find.
<tb>
<I> Example: </I>
<tb> 14 <SEP> g <SEP> Xndlrostanorn (3) -o @ l-acetate- (17) <SEP> from
<tb> Smp. <SEP> 157 <SEP> are <SEP> dissolved in <SEP> 10 <SEP> cm @ <SEP> glacial acetic acid <SEP>
<tb> and <SEP> at <SEP> room temperature <SEP> after <SEP> addition <SEP> of
<tb> a few <SEP> drops of <SEP> hydrogen bromide glacial acetic acid
<tb> in the <SEP> run <SEP> one <SEP> half an <SEP> hour <SEP> with <SEP> one <SEP> solution, <SEP> from <SEP> 4.28 <SEP> em # < SEP> bromine <SEP> in <SEP> 250, em '<SEP> ice cream
<tb> under <SEP> stirring <SEP> linked. <SEP> The <SEP> decolorized <SEP> solution
<tb> <SEP> is carefully sprayed <SEP> with <SEP> water <SEP>, <SEP> whereby
<tb> the <SEP> raw <SEP> 2,4-dibromo-androstanoliacetat- (17) -
EMI0001.0004
on;
- (3) <SEP> flocculates <SEP> and <SEP> agglomerates <SEP>.
<tb> After <SEP> some <SEP> standing <SEP> <SEP> one <SEP> filters <SEP> raw product <SEP> from <SEP> and <SEP> crystallizes <SEP> it <SEP> from < SEP> alcohol
<tb> around. <SEP> The <SEP> pure <SEP> .2,4-Dibmom.-ankostanoliac: etat (17) -on- (3,) <SEP> crystallizes <SEP> from <SEP> alcohol <SEP> in <SEP > colorless <SEP> needles, <SEP> the <SEP> at <SEP> 194 <SEP> under <SEP> decomposition
<tb> melt. <SEP> yield <SEP> 11.4 <SEP> g.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE228433X | 1940-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228433A true CH228433A (en) | 1943-08-31 |
Family
ID=5867187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228433D CH228433A (en) | 1940-02-03 | 1941-01-31 | Process for the preparation of 2,4-dibromo-androstanol acetate- (17) -one- (3). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228433A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715637A (en) * | 1950-01-23 | 1955-08-16 | Syntex Sa | Process for producing detla4-3-ketosteroids and intermediates thereof |
-
1941
- 1941-01-31 CH CH228433D patent/CH228433A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715637A (en) * | 1950-01-23 | 1955-08-16 | Syntex Sa | Process for producing detla4-3-ketosteroids and intermediates thereof |
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