Reacción #573668

Ecuación de reacción

Methyl (RS)-4-cyano-2-phenylbutanoate

tri-n-butyltin azide

hydrogen chloride

→

title compound

Rendimiento 61.0%

Methyl (RS)-2-phenyl-4-(1H-tetrazol-5-yl)butanoate

Rendimiento 61.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroEvaporation
2. 2
   Otrogave a residue which
3. 3
   Otrowas triturated three times with diisopropyl ether
4. 4
   Otrothen partitioned between 10% aqueous sodium carbonate and ethyl acetate
5. 5
   Extracciónextracted with ethyl acetate
6. 6
   SecadoThe organic layer was dried over magnesium sulphate
7. 7
   Otroevaporated

Procedimiento

Methyl (RS)-4-cyano-2-phenylbutanoate (see Preparation 21) (1.8 g) and tri-n-butyltin azide (3.23 g were mixed and heated at 160° C. for 3 hours, dissolved in methanol (100 ml), treated by the addition of hydrogen chloride gas for 10 minutes and left for 18 hours. Evaporation gave a residue which was triturated three times with diisopropyl ether then partitioned between 10% aqueous sodium carbonate and ethyl acetate. The aqueous later was acidifed with 2 M hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and evaporated to give the title compound (1.34 g, 61%) as a brown oil.

Fuente