t-Butyl (S)-5-benzyloxy-3-oxononanoate → t-Butyl (3S,5S)-5-benzyloxy-3-hydroxynonanoate

Participants

Reaction Steps

In a 500 ml autoclave were charged 95 ml of dried methanol, 22.0 g of the compound obtained in Step 2, and 0.634 g of (S)-iodo-π-p-cymene[2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium iodide in a nitrogen stream, and the mixture was allowed to react at room temperature under a hydrogen pressure of 75 to 80 kg/cm2 for 18 hours. The solvent was removed by distillation under reduced pressure to obtain 22.3 g of a crude product. Purification by silica gel column chromatography gave 16.3 g (73.4%) of the titled compound.

Provenance & Evidence