Reacción #790461

Ecuación de reacción

methylene chloride

methyl 2-(N-benzoylamino)methyl-3-oxobutanoate

→

methyl (2R, 3S)-2-(N-benzoylamino)methyl-3-hydroxybutanoate

Rendimiento 91.0%

Disolventes

NEt3

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed by distillation under reduced pressure of 20 mmHg at 30° C
2. 2
   OtroThe residue was purified by silica gel column chromatography
3. 3
   workup.ADDITIONa 7/3 (by volume) mixture of hexane and isopropanol as an eluent

Procedimiento

In a 100 ml-volume autoclave whose atmosphere had been displaced with nitrogen was added a methylene chloride solution of 2.5 g of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of Ru2Cl4 ((-)-BINAP2 (NEt3), and a reaction was conducted by stirring at 45° C. under a hydrogen pressure of 70 kg/cm2 for 24 hours. The reaction mixture was taken out, and the solvent was removed by distillation under reduced pressure of 20 mmHg at 30° C. The residue was purified by silica gel column chromatography using a 7/3 (by volume) mixture of hexane and isopropanol as an eluent to obtain 2.27 g (yield: 91%) of methyl (2R, 3S)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 97 %ee.

Fuente