3-Oxooctanoic acid t-butyl ester → (R)-3-hydroxyoctanoic acid t-butyl ester

Participants

Reaction Steps

The 3-oxooctanoic acid t-butyl ester (4.50 g, 21.0 mmol) obtained in Production Example A-1 and dichloro [(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium (II) (hereunder abbreviated as (R)-BINAP-RuCl2) (40 mg, 50.3 μmol) were dissolved in methanol (10 ml) freeze-degassed with liquid nitrogen. The obtained methanol solution was stirred for 42 hours using an autoclave (SUS-316; Taiatsu) at room temperature under 60 atm of hydrogen. The reaction solution was then condensed, and purified using column chromatography (silica gel: 150 g, n-hexane/ethyl acetate=10/1) to produce the target compound (4.11 g, 89%).

Provenance & Evidence