BE836488R - PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE AJMALICIN AND EPI-19-AJMALICIN - Google Patents
PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE AJMALICIN AND EPI-19-AJMALICINInfo
- Publication number
- BE836488R BE836488R BE162618A BE162618A BE836488R BE 836488 R BE836488 R BE 836488R BE 162618 A BE162618 A BE 162618A BE 162618 A BE162618 A BE 162618A BE 836488 R BE836488 R BE 836488R
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- formula
- product
- ajmalicin
- iii
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<EMI ID=1.1>
La présente invention concerne un procédé de
<EMI ID=2.1>
L'invention vise à obtenir* ces* deux 'composés avec de meilleurs rendements.
A cet effet, au lieu de cycliser la déméthylcorynanthéine, on effectue la cyclisation directement sur la
<EMI ID=3.1>
<EMI ID=4.1>
Dans une première forme de réalisation du
<EMI ID=5.1>
obtenir un mélange d'Isomères optiques de formule
<EMI ID=6.1>
<EMI ID=7.1>
obtenir le produit méthylé correspondant de formule
<EMI ID=8.1>
...........
et on déshydrate le produit de fcrmule (III) en ajmaiieine de formule
<EMI ID=9.1>
et épi-19-ajmalicine de formule
<EMI ID=10.1>
Dans une deuxième forme de réalisation du procédé, on effectue la cyclisation de la corynanthéine directement en produit de formule (III) et on transforme
<EMI ID=11.1>
L'ensemble du procéda peut être représenté à l'aide du schéma suivant
<EMI ID=12.1>
<EMI ID=13.1> de l'Invention sont atteints de la façon suivante
<EMI ID=14.1>
<EMI ID=15.1>
anhydre, puis filtrée et évaporée.
<EMI ID=16.1>
soude, puis filtrée* on dilue la solution par de l'eau, puis on évapore le aéthanol par distillation sons vide.
La solution aqueuse est extraite par un solvant non miscible
19 eau tel que le chlorure de méthylène on le chloroforme.
La phase organique est décantée, lavée par de l'eau et
<EMI ID=17.1>
évaporée.
Dans le troisième stade, le produit il=) tenu
<EMI ID=18.1>
solution aqueuse de carbonate de sodium, puis on "trait par <EMI ID=19.1>
Pour obtenir chacun de ces produits, le
<EMI ID=20.1>
<EMI ID=21.1>
<EMI ID=22.1>
les exemples suivants illustrent de façon
<EMI ID=23.1>
<EMI ID=24.1> <EMI ID=25.1>
On agite 1 heure, filtre sur eélite puis on extrait par le chloroforme. Par évaporation à sec, on obtient 5,6 g d'un produit qui aéra méthylé.
<EMI ID=26.1>
<EMI ID=27.1>
<EMI ID=28.1>
On porte à reflux 20 heures.
Après refroidissement, on alcalinise
par la soude, puis on filtre. On concentre la solution
puis on extrait par le chlorure de méthylène. La méthylation
<EMI ID=29.1>
<EMI ID=30.1>
laires.
<EMI ID=31.1>
<EMI ID=32.1>
on obtient 2,985 g de produit (III), dérivé
<EMI ID=33.1> <EMI ID=34.1>
Les produits ainsi obtenus sont identi-
<EMI ID=35.1>
brevet principal.
<EMI ID=36.1>
et 50 ml d'eau.
<EMI ID=37.1>
<EMI ID=38.1>
<EMI ID=39.1>
et on ajoute goutte à goutte 86 ml de soude caustique 3M. On agita pendant 1 heure, filtre sur célite, puis extrait par le chloroforme. Par évaporation à sec, on obtient 5,875 CI de produit (III) tel que décrit dans la référence de littérature indiquée précéderaient.
<EMI ID=40.1>
On ajoute au mélange issu du stade A
<EMI ID=41.1>
<EMI ID=42.1> <EMI ID=43.1>
carbonate de sodium* puis on extrait par l'éther*
<EMI ID=44.1> <EMI ID=45.1> <EMI ID=46.1> <EMI ID=47.1>
<EMI ID=48.1>
<EMI ID=49.1>
pal.
<EMI ID=50.1>
<EMI ID = 1.1>
The present invention relates to a method of
<EMI ID = 2.1>
The invention aims to obtain * these * two 'compounds with better yields.
To this end, instead of cyclizing the demethylcorynantheine, the cyclization is carried out directly on the
<EMI ID = 3.1>
<EMI ID = 4.1>
In a first embodiment of the
<EMI ID = 5.1>
obtain a mixture of optical isomers of formula
<EMI ID = 6.1>
<EMI ID = 7.1>
obtain the corresponding methylated product of formula
<EMI ID = 8.1>
...........
and the product of formula (III) is dehydrated into an additive of formula
<EMI ID = 9.1>
and epi-19-ajmalicin of formula
<EMI ID = 10.1>
In a second embodiment of the process, the cyclization of corynanthein is carried out directly into the product of formula (III) and
<EMI ID = 11.1>
The whole process can be represented using the following diagram
<EMI ID = 12.1>
<EMI ID = 13.1> of the Invention are achieved as follows
<EMI ID = 14.1>
<EMI ID = 15.1>
anhydrous, then filtered and evaporated.
<EMI ID = 16.1>
sodium hydroxide, then filtered * the solution is diluted with water, then the ethanol is evaporated off by vacuum distillation.
The aqueous solution is extracted with an immiscible solvent
19 water such as methylene chloride or chloroform.
The organic phase is decanted, washed with water and
<EMI ID = 17.1>
evaporated.
In the third stage, the product he =) held
<EMI ID = 18.1>
aqueous sodium carbonate solution, then "treated with <EMI ID = 19.1>
To obtain each of these products, the
<EMI ID = 20.1>
<EMI ID = 21.1>
<EMI ID = 22.1>
the following examples illustrate how
<EMI ID = 23.1>
<EMI ID = 24.1> <EMI ID = 25.1>
Stirred 1 hour, filtered on elite and then extracted with chloroform. By evaporation to dryness, 5.6 g of a product which aerated methyl is obtained.
<EMI ID = 26.1>
<EMI ID = 27.1>
<EMI ID = 28.1>
It is brought to reflux for 20 hours.
After cooling, alkalinizes
by soda, then filtered. We concentrate the solution
then extracted with methylene chloride. Methylation
<EMI ID = 29.1>
<EMI ID = 30.1>
laires.
<EMI ID = 31.1>
<EMI ID = 32.1>
2.985 g of product (III) is obtained, derivative
<EMI ID = 33.1> <EMI ID = 34.1>
The products thus obtained are identified
<EMI ID = 35.1>
main patent.
<EMI ID = 36.1>
and 50 ml of water.
<EMI ID = 37.1>
<EMI ID = 38.1>
<EMI ID = 39.1>
and 86 ml of 3M caustic soda are added dropwise. Stirred for 1 hour, filtered through Celite, then extracted with chloroform. By evaporation to dryness, 5.875 CI of product (III) is obtained as described in the literature reference indicated above.
<EMI ID = 40.1>
To the mixture resulting from stage A is added
<EMI ID = 41.1>
<EMI ID = 42.1> <EMI ID = 43.1>
sodium carbonate * then extracted with ether *
<EMI ID = 44.1> <EMI ID = 45.1> <EMI ID = 46.1> <EMI ID = 47.1>
<EMI ID = 48.1>
<EMI ID = 49.1>
pal.
<EMI ID = 50.1>
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE162618A BE836488R (en) | 1975-12-10 | 1975-12-10 | PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE AJMALICIN AND EPI-19-AJMALICIN |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE162618A BE836488R (en) | 1975-12-10 | 1975-12-10 | PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE AJMALICIN AND EPI-19-AJMALICIN |
BE836488 | 1975-12-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
BE836488R true BE836488R (en) | 1976-04-01 |
Family
ID=25649004
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE162618A BE836488R (en) | 1975-12-10 | 1975-12-10 | PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE AJMALICIN AND EPI-19-AJMALICIN |
Country Status (1)
Country | Link |
---|---|
BE (1) | BE836488R (en) |
-
1975
- 1975-12-10 BE BE162618A patent/BE836488R/en not_active IP Right Cessation
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
RE | Patent lapsed |
Owner name: OMNIUM CHIMIQUE S.A. Effective date: 19861231 |
|
RE | Patent lapsed |
Owner name: OMNIUM CHIMIQUE S.A. Effective date: 19881231 |