8-Hydroxy-6-oxo-octanoic acid methyl ester → Methyl (6S)-6,8-dihydroxyoctanoate

Participants

Reaction Steps

A 100 ml autoclave was charged under argon with 3.8 g (20 mmol) of 8-hydroxy-6-oxo-octanoic acid methyl ester, with the Ru-(S)-BINAP catalyst solution prepared under Example 2, and with 20 ml of oxygen-free methanol. The hydrogenation was carried out for 20 hours at 60° C., at a constant pressure of 40 bar pure H2 and with intensive stirring. When the reaction was complete, the solvent was distilled off using a rotary evaporator. Purification of the residue by column chromatography (silica gel, ethyl acetate/n-hexane) yielded 3.1 g (82%) of (S)-6,8-dihydroxyoctanoic acid methyl ester having an enantiomeric excess of 96% (chiral GC).

Provenance & Evidence