Methyl 2-((benzoylamino)methyl)-3-oxobutanoate → (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

Participants

Reaction Steps

In a 100 ml-volume stainless steel autoclave whose atmosphere had been displaced with nitrogen was added a solution of 2.5 g (10 mmole) of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 184 mg (0.1 mmole) of [Ru((+)BINAP)](CLO4)2 in 18 ml of dichloroethane, and a reaction was conducted at 70° C. under a hydrogen pressure of 100 kg/cm2 for 30 hours. The reaction mixture was concentrated under reduced pressure of 20 mmHg, and the residue was purified by silica gel column chromatography using a 7/3 (by volume) mixture of hexane and isopropanol as an eluent to give 2.19 g (yield: 86.5%) of methyl (2S, 3R)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 90 %ee.

Provenance & Evidence