ChemicalBook CAS DataBase List VIGABATRIN

VIGABATRIN synthesis

6synthesis methods

Product Name:VIGABATRIN
CAS Number:60643-86-9
Molecular formula:C6H11NO2
Molecular Weight:129.16

Vigabatrin, also known as gamma-vinyl-GABA, is an antiepileptic drug that inhibits the breakdown of γ-aminobutyric acid (GABA) by acting as a suicide inhibitor of GABA transaminase (GABA-T). It is a structural analog of GABA, but does not bind to GABA receptors. Vigabatrin is an irreversible suicide inhibitor of gamma-aminobutyric acid transaminase (GABA-T), the enzyme responsible for the catabolism of GABA, which increases the level of GABA in the brain. Vigabatrin is a racemic compound, and its [S]-enantiomer is pharmacologically active.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

Deleris, G.; Dunogues, J.; Gadras, A. Direct regiospecific allylic amination via silicon induced pericyclic reactions. A novel synthesis of gamma vinyl GABA. Tetrahedron. Volume 44. Issue 13. Pages 4243-58. 1988.

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60643-86-9
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Yield:60643-86-9 60%

Reaction Conditions:

Stage #1:5(S)-Vinyl-2-Pyrrolidinone with water;potassium hydroxide in isopropyl alcohol at 20 - 60; for 16 h;Inert atmosphere;
Stage #2: with acetic acid in water;isopropyl alcohol

Steps:

c
Step c) 5-vinyl-2-pyrrolidone (III) hydrolysis to 4-amino-5-hexenoic acid (I): 5-vinyl-2-pyrrolidone (III) can be hydrolyzed to 4-amino-5-hexenoic acid of formula (I), according to one of the two procedures described in or . Under argon, 1 g of 5-vinyl-2-pyrrolidone (6 mmol) is dissolved in a mixture of isopropanol (10 ml) and deionized water (1 ml). To this solution, 0.9 g of potassium hydroxide is added at room temperature and the mixture is then heated at 60°C for 16 h. After cooling, the reaction is quenched with 1 ml of glacial acetic acid and crude 4-amino-5-hexenoic acid precipitates in the reaction mixture. 4-amino-5-hexenoic acid is recovered by filtration and recrystallized in a mixture of water/isopropanol to give 700 mg of white 4-amino-5-hexenoic acid crystals (60 % yield).

References:

Targeon SAS EP2537827, 2012, A1 Location in patent:Page/Page column 9

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