Reacción #1677951

Ecuación de reacción

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate

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title compound

Rendimiento 90.0%

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

Rendimiento 90.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA solution was prepared
2. 2
   Otroprepared
3. 3
   OtroReaction
4. 4
   Otroto proceed at 50° C., under a hydrogen
5. 5
   Otrofor 20 hours
6. 6
   workup.DISTILLATIONThe solvent was distilled off
7. 7
   workup.ADDITIONthe remainder was subjected to the silica gel column chromatography (eluent; mixture of n-hexane and ethyl acetate) for removal of the catalyst

Procedimiento

A solution was prepared by dissolving 2.5 g (10 mmol) of methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate and 84.5 mg (0.05 mmol) of the ruthenium-optically active phosphine complex prepared by following the general procedures of Referential Example 1 (Ru2Cl4 ((+)-BINAP)2 (NEt3)) in 17.5 ml of methylene chloride. The solution was placed in a 100 ml stainless steel autoclave wherein the inside air was replaced with nitrogen gas in advance. Reaction was allowed to proceed at 50° C., under a hydrogen pressure of 100 kg/cm2 for 20 hours under stirring. The solvent was distilled off and the remainder was subjected to the silica gel column chromatography (eluent; mixture of n-hexane and ethyl acetate) for removal of the catalyst to obtain 2.25 g of the title compound (yield: 90%, optical purity: 98% ee). To determine the optical purity, the compound was further derived to an ester of (+)-α-methoxy-α-trifluoromethylphenyl acetic acid, then applied to high performance liquid chromatography (column; Develosil® 100-3(4.6 mm×250 mm), manufactured by Nomura Kagaku K.K.; wave length (UV): 254 nm; eluent: hexane/diethylether=90/10; flow rate: 1 ml/min).

Fuente