ChemicalBook CAS DataBase List 4-Aminobutyric acid

4-Aminobutyric acid synthesis

14synthesis methods

Product Name:4-Aminobutyric acid
CAS Number:56-12-2
Molecular formula:C4H9NO2
Molecular Weight:103.12

The synthesis of 4-aminobutyric acid mainly includes the following: the first is the use of potassium Phthaloyl imine and γ- Chloroprene cyanogen or butyrolactone is used as the raw material of GABA. The final product obtained after violent reaction and hydrolysis is GABA; The second is to use pyrrolidone as the initial raw material, hydrolyze it through calcium hydroxide and ammonium bicarbonate, and finally open its ring to obtain GABA; The third is to use butyric acid and ammonia as raw materials of GABA γ GABA was obtained by light reaction under X-ray conditions; The fourth method is to synthesize GABA with propylamine and formic acid by glow discharge; The fifth is to use methyl bromoacetate and ethylene as raw materials to prepare GABA. Methyl 4-bromobutyrate is obtained through polymerization. Finally, the product after ammonolysis and hydrolysis is GABA. The chemical synthesis methods of GABA have the disadvantages of difficult reaction control and high cost.

21994-40-1
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56-12-2
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Yield:-

Reaction Conditions:

Stage #1: 4-azidobutanenitrilewith trisodium thiophosphate in water-d2 at 90; for 3 h;
Stage #2: with [D]-sodium hydroxide in water-d2 at 90; for 16 h;

Steps:

Experimental procedures for entries in Table 2

Entry 8: Trisodium thiophosphate (140 μmol, 25 mg) was dissolved in D2O (1 mL) and the solution was added to 4-azido-butyronitrile (45 μmol, 5 mg) in an NMR tube. The NMR tube was heated at 90 °C for 3 h, and allowed to cool. 100 μl of 40% sodium deuteroxide in deuterium oxide was added to the NMR tube, and was heated at 90 °C for 3 h before being subjected to 1H, 13C NMR analyses. To confirm the formation of γ-aminobutyric acid, commercial GABA was added to the NMR tube, with 1H and 13C NMR analyses being performed after addition.

References:

Norcliffe, Jennifer L.;Conway, Louis P.;Hodgson, David R.W. [Tetrahedron Letters,2011,vol. 52,# 21,p. 2730 - 2732] Location in patent:supporting information; body text

Spiro[2,4-benzodioxepin-3,1'-cyclopropane]-2'-carbonitrile, 1,5-dihydro-

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56-12-2
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References

21994-40-1
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616-45-5 Synthesis

616-45-5
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56-12-2
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References

56-86-0 Synthesis

56-86-0
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56-12-2
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References

80127-29-3 Synthesis

(S)-4-[(Allyloxycarbonyl)amino]butanoic acid

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References

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