SU523108A1 - The method of obtaining 17, 20,20,21-bismethylenedioxy-6-methylenehydrocortisone - Google Patents
The method of obtaining 17, 20,20,21-bismethylenedioxy-6-methylenehydrocortisoneInfo
- Publication number
- SU523108A1 SU523108A1 SU2106916A SU2106916A SU523108A1 SU 523108 A1 SU523108 A1 SU 523108A1 SU 2106916 A SU2106916 A SU 2106916A SU 2106916 A SU2106916 A SU 2106916A SU 523108 A1 SU523108 A1 SU 523108A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methylenedioxy
- methylenehydrocortisone
- obtaining
- bismethylenedioxy
- bis
- Prior art date
Links
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к усовершенствованию способа получени 17сс,20,20,21-бис-метилендиоксипроизводного 6-метиленгидрокортизона , вл ющегос промежуточным веществом в синтезе урбазона - важного противовоспалительного препарата.The invention relates to the improvement of the method of obtaining 17cc, 20,20,21-bis-methylenedioxy derivative of 6-methylenehydrocortisone, which is an intermediate substance in the synthesis of urbazone - an important anti-inflammatory drug.
Известен способ получени 17а,20,20,21бис - метилендиоксипроизводного 6-метиленгидрокортизона из 17а,20,20,21-б«с-метилепдиокси-3-этоксипрегнадиен - 3,5-она-11 путем последовательного восстановлени 11-кетогрунпы боргидридом натри , формилировани с помощью реактива Вильсмейера, повторного восстановлени боргидридом натри 6-формильной группы, дегидратации и гидролиза полученного при этом карбинола в целевой продукт 1.A known method for preparing 17a, 20,20,21 bis - methylenedioxy 6-methylene hydrocortisone from 17a, 20,20,21-b "c-methylepdioxy-3-ethoxypregnadien-3,5-one-11" by successive reduction of 11-keto-grnpa with sodium borohydride formulating with Vilsmeier reagent; re-reducing sodium 6-formyl group with sodium borohydride; dehydrating and hydrolyzing the resulting carbinol to the desired product 1.
Однако при известном способе процесс протекает с больщим числом стадий, боргидрид натри используетс дл восстановлени на двух стади х и формилироваиие с помощью реактива Вильсмейера проводитс на соединении , содержащем свободную 11-оксигруппу, согласно же литературным данным 2 реакци Вильсмейера осложн етс р дом побочных процессов - дегидратацией и формилированием П-оксигруппы, что обычно приводит к снижению выхода формильного производного . С целью упрощени процесса за счет сокращени числа химических стадий и However, with the known method, the process proceeds with a large number of stages, sodium borohydride is used for reduction in two stages and the formilation with Vilsmeier reagent is carried out on a compound containing a free 11-hydroxy group, according to the literature data, the 2 Vilsmeier reaction is complicated by a number of side processes - dehydration and formylation of the P-hydroxy groups, which usually leads to a decrease in the yield of the formyl derivative. In order to simplify the process by reducing the number of chemical steps and
уменьшени побочных процессов по предлагаемому способу формилированию подвергают непосредственно 17а,20,20,21-бис-метилендиокси-3-метоксипрегнадиен - 3,5 - она - 11, а гидрирование образующегос дикарбонильного соединени осуществл ют на второй стадии . Известны и другие аналогичные способы получени целевого продукта 3,4.17a, 20,20,21-bis-methylenedioxy-3-methoxypregnadiene-3,5-she-11 is directly subjected to the reduction of side processes in the proposed method, and the hydrogenation of the resulting dicarbonyl compound is carried out in the second stage. Other similar methods are known for the preparation of the target product 3.4.
Описываетс способ получени 17а,20,20, 21-быс - метилендиоксипроизводного 6-метнленгидрокортизона путем формилировани 17а,20,20,21 - бис - метилендиокси-3-метоксипрегнадиен-3 ,5-она-11 с помощью реактива Вильсмейера, с последующим гидрированием боргидридом натри образующегос дикарбонильного соединени .Describes how to obtain 17a, 20,20, 21-by-methylenedioxy 6-methlenhydrocortisone by formylation 17a, 20,20,21-bis-methylenedioxy-3-methoxyprednadien-3, 5-one-11 using Vilsmeier reagent, followed by hydrogenation sodium borohydride of the resulting dicarbonyl compound.
Из 17а,20,20,21-бис - метилендиокси-3-метоксипрегнадиен-3 ,5-она-11 реакцией Вильсмейера получают 6-формильное производное, при восстановлении которого борогидридом натри образуетс 11-окси- и 6-оксиметпльпое , которое без выделени подвергаетс дегидратации и гидролизу с выделением целевого продукта.From 17a, 20,20,21-bis-methylenedioxy-3-methoxypregnadien-3, 5-one-11, the Vilsmeier reaction yields a 6-formyl derivative, which, upon reduction with sodium borohydride, forms 11-hydroxy- and 6-hydroxymethyl, which without release of dehydrated and hydrolyzed to release the desired product.
Использование в качестве исходного соединени 17а,20,20,21-бис - метилендиокси-3-метоксипрегнадиен-3 ,5-она-11 позвол ет избежать образование побочных веществ на стадии введени формильной труппы по реакции Вильсмейера.The use of starting compounds 17a, 20,20,21-bis-methylenedioxy-3-methoxypregnadien-3, 5-one-11 allows to avoid the formation of side substances at the stage of introduction of the formyl group by the reaction of Vilsmeier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2106916A SU523108A1 (en) | 1975-02-21 | 1975-02-21 | The method of obtaining 17, 20,20,21-bismethylenedioxy-6-methylenehydrocortisone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2106916A SU523108A1 (en) | 1975-02-21 | 1975-02-21 | The method of obtaining 17, 20,20,21-bismethylenedioxy-6-methylenehydrocortisone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU523108A1 true SU523108A1 (en) | 1976-07-30 |
Family
ID=20610648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2106916A SU523108A1 (en) | 1975-02-21 | 1975-02-21 | The method of obtaining 17, 20,20,21-bismethylenedioxy-6-methylenehydrocortisone |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU523108A1 (en) |
-
1975
- 1975-02-21 SU SU2106916A patent/SU523108A1/en active
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