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  • Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: a short route to γ-aminobutyric acid esters.

Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: a short route to γ-aminobutyric acid esters.

The Journal of organic chemistry (2012-07-11)
Michael R Emmett, Huck K Grover, Michael A Kerr
ABSTRACT

Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce γ-azidobutyric acids in good yields. These adducts were hydrogenated to form γ-aminobutyric acid (GABA) methyl esters.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium azide 0.1 M solution
Sigma-Aldrich
Sodium azide, BioUltra, ≥99.5% (T)
Sigma-Aldrich
Sodium azide, BioXtra
Sigma-Aldrich
Sodium azide, ReagentPlus®, ≥99.5%
Sigma-Aldrich
Sodium azide, purum p.a., ≥99.0% (T)
Sigma-Aldrich
Methyl 4-aminobutyrate hydrochloride, ≥99.0% (AT)