Reacción #2273674

ord-0d3ab2c3eb3b43be9d54cb0bcb994bc8

Ecuación de reacción

COC(=O)C(CNC(=O)c1ccccc1)C(C)=O
methyl-2-(N-benzoylamino)methyl-3-oxobutyrate
CCN(CC)CC
NEt3
COC(=O)[C@@H](CNC(=O)c1ccccc1)[C@@H](C)O
title compound
Rendimiento 90.0%
COC(=O)[C@@H](CNC(=O)c1ccccc1)[C@@H](C)O
methyl (2S,3R)-2-(N-benzoylamino)methyl-3-hydroxybutyrate
Rendimiento 90.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was removed by evaporation under reduced pressure
  2. 2
    Otrothe residue was purified by column chromatography

Procedimiento

In a 100 ml autoclave was put a solution of 2.5 g (10 mmol) of methyl-2-(N-benzoylamino)methyl-3-oxobutyrate and 173 mg (0.102 mmol) of Ru2Cl4((R)-BINAP)2.NEt3 in 17.5 ml of methylene chloride, and the mixture was stirred at 50° C. under a hydrogen pressure of 10000 kPa for 20 hours. The solvent was removed by evaporation under reduced pressure, and the residue was purified by column chromatography to furnish 2.25 g (90%) of the title compound. Optical purity: 98%e.e.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06403804B1uspto-grants-2002_06