Reacción #790455

Ecuación de reacción

Ru2Cl4 ((+)-BINAP)2

NEt3

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

→

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

Rendimiento 90.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa hydrogenation reaction
2. 2
   OtroThe solvent was removed from the reaction mixture by distillation
3. 3
   Otrothe residue was purified by silica gel column chromatography

Procedimiento

In a 100 ml-volume stainless steel-made autoclave whose atmosphere had been displaced with nitrogen was charged a solution of 2.5 g (10 mmole) of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of the ruthenium-optically active phosphine complex as synthesized in Reference Example 1 [Ru2Cl4 ((+)-BINAP)2 (NEt3)] in 17.5 ml of methylene chloride, and the mixture was stirred at 50° C. under a hydrogen pressure of 100 kg/cm2 for 20 hours to conduct a hydrogenation reaction. The solvent was removed from the reaction mixture by distillation, and the residue was purified by silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate as an eluent to obtain 2.25 g (yield: 90%) of methyl (2S, 3R)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 98 %ee.

Fuente