Methyl Acetate → HCID 57144588, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate synthesized in the same manner as in Example 5, except for replacing t-butyl acetate with methyl acetate was used. That is, 16.9 mg (0.01 mmole) of Ru2Cl4 ((R)-BINAP)2 (NEt3) was weighed, and 500 mg (2.15 mmole) of methyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate and 50 ml of methanol were added thereto to form a solution. The solution was transferred to a 100 ml-volume autoclave whose atmosphere had been displaced with nitrogen, and the solution was stirred at 30° C. for 21 hours under a hydrogen pressure of 50 kg/cm2 to conduct hydrogenation. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography (diethyl ether/hexane: 5/1 by volume) to obtain 323 mg (yield: 65%) of methyl (3R,5S)-6-t-butoxy-3,5-dihydroxyhexanoate.

Provenance & Evidence