AR064949A1 - A PROCEDURE FOR PREGABALINE PREPARATION - Google Patents
A PROCEDURE FOR PREGABALINE PREPARATIONInfo
- Publication number
- AR064949A1 AR064949A1 ARP080100219A AR064949A1 AR 064949 A1 AR064949 A1 AR 064949A1 AR P080100219 A ARP080100219 A AR P080100219A AR 064949 A1 AR064949 A1 AR 064949A1
- Authority
- AR
- Argentina
- Prior art keywords
- methyl
- acid
- nitro
- hexanoic acid
- malonate
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Se provee un procedimiento para la preparacion de pregabalina, el cual comprende: (a) someter a una reaccion de Vilsmeier al compuesto 4-metil pentan-2-ona con oxicloruro de fosforo en presencia de dimetilformamida, para obtener 3-cloro-5-metil hex- 2-enal, (b) someter al 3-cloro- 5-metil hex-2-enal a una oxidacion con trioxido de cromo, para obtener el ácido 3-cloro-5-metil hex-2-enoico, (c) someter al ácido 3-cloro-5-metil hex-2-enoico a un acoplamiento de sonogashira con nitrometano, para obtener el ácido 5-metil-3-(nitro metil) hexenoico, (d) reducir el ácido 5-metil-3-(nitrometil) hexenoico con una reduccion catalítica leve, para obtener el ácido 5-metil-3-(nitrometil) hexenoico con una pureza enantiomérica mayor al 99,9%, (e) realizar la resolucion del ácido 5-metil-3-(nitro metil) hexanoico con un agente de resolucion, tal como una base auxiliar quiral, para obtener el ácido 3(S)-5-metil-3-(nitro metil) hexanoico y (f) reducir el ácido 3(S)-5-metil-3-(nitro metil) hexanoico para obtener el ácido 3(S)-5-metil-3-(amino metil) hexanoico, con una pureza enantiomérica mayor al 99,9%. También se provee un procedimiento para la preparacion de pregabalina, el cual comprende: (a) hacer reaccionar 3-Metil butanal con dietilmalonato en presencia de una base, para obtener dietil (3-metilbutiliden)malonato, (b) someter al dietil (3-etilbutiliden)malonato una reaccion de Michael con nitrometano, para obtener un dietil [3-metil-1-(nitrometil)butil] malonato, (c) someter a hidrolisis y a descarboxilacion al dietil [3-metil-1-(nitrometil)butil]malonato en presencia de una base fuerte en alcoholes primarios, para obtener el ácido 5-metil-3-(nitro metil) hexanoico, (d) resolver el ácido 5-metil-3-(nitro metil) hexanoico con un agente de resolucion tal como una base auxiliar quiral, para obtener el ácido 3(S)-3-(nitro metil)-5-metil hexanoico con una pureza enantiomérica mayor al 99,9% y (e) reducir el ácido 3(S)-3-(nitrometil)-5-metil hexanoico con reduccion catalítica, para obtener un ácido 3(S)-3-(aminometil)-5-metil hexanoico con una pureza enantiomérica mayor al 99,9%.A process for the preparation of pregabalin is provided, which comprises: (a) undergoing a Vilsmeier reaction to the 4-methyl pentan-2-one compound with phosphorus oxychloride in the presence of dimethylformamide, to obtain 3-chloro-5- methyl hex-2-enal, (b) subject 3-chloro-5-methyl hex-2-enal to oxidation with chromium trioxide, to obtain 3-chloro-5-methyl hex-2-enoic acid, ( c) subject 3-chloro-5-methyl hex-2-enoic acid to a coupling of sonogashira with nitromethane, to obtain 5-methyl-3- (nitro methyl) hexenoic acid, (d) reduce 5-methyl acid -3- (nitrometil) hexenoic acid with a slight catalytic reduction, to obtain 5-methyl-3- (nitrometyl) hexenoic acid with an enantiomeric purity greater than 99.9%, (e) perform the resolution of 5-methyl acid- 3- (nitro methyl) hexanoic acid with a resolving agent, such as a chiral auxiliary base, to obtain 3 (S) -5-methyl-3- (nitro methyl) hexanoic acid and (f) reduce acid 3 (S ) -5-methyl-3- (nitro methyl) hexa noic to obtain 3 (S) -5-methyl-3- (amino methyl) hexanoic acid, with an enantiomeric purity greater than 99.9%. A process for the preparation of pregabalin is also provided, which comprises: (a) reacting 3-Methyl butanal with diethylmalonate in the presence of a base, to obtain diethyl (3-methylbutylidene) malonate, (b) subject to diethyl (3 -ethylbutylidene) malonate a reaction of Michael with nitromethane, to obtain a diethyl [3-methyl-1- (nitromethyl) butyl] malonate, (c) subject to hydrolysis and decarboxylation to diethyl [3-methyl-1- (nitromethyl) butyl ] malonate in the presence of a strong base in primary alcohols, to obtain 5-methyl-3- (nitro methyl) hexanoic acid, (d) solve 5-methyl-3- (nitro methyl) hexanoic acid with a resolving agent such as a chiral auxiliary base, to obtain 3 (S) -3- (nitro methyl) -5-methyl hexanoic acid with an enantiomeric purity greater than 99.9% and (e) reduce acid 3 (S) -3 - (nitrometil) -5-methyl hexanoic acid with catalytic reduction, to obtain a 3 (S) -3- (aminomethyl) -5-methyl hexanoic acid with an enantiomeric purity greater than 99, 9%
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ARP080100219 AR064949A1 (en) | 2008-01-17 | 2008-01-17 | A PROCEDURE FOR PREGABALINE PREPARATION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ARP080100219 AR064949A1 (en) | 2008-01-17 | 2008-01-17 | A PROCEDURE FOR PREGABALINE PREPARATION |
Publications (1)
Publication Number | Publication Date |
---|---|
AR064949A1 true AR064949A1 (en) | 2009-05-06 |
Family
ID=40673047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP080100219 AR064949A1 (en) | 2008-01-17 | 2008-01-17 | A PROCEDURE FOR PREGABALINE PREPARATION |
Country Status (1)
Country | Link |
---|---|
AR (1) | AR064949A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9745249B2 (en) | 2014-06-12 | 2017-08-29 | Siegfried Ltd. | Method for the preparation of beta-substituted gamma-amino carboxylic acids |
-
2008
- 2008-01-17 AR ARP080100219 patent/AR064949A1/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9745249B2 (en) | 2014-06-12 | 2017-08-29 | Siegfried Ltd. | Method for the preparation of beta-substituted gamma-amino carboxylic acids |
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