HCID 57137252, compound → HCID 57120352, compound

Participants

Reaction Conditions

Reaction Steps

In the same manner as in Example 5, 15.8 mg (0.009 mmole) of Ru2Cl4 ((S)-Tol-BINAP)2 (NEt3) was weighed, and 500 mg (1.75 mmole) of t-butyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate as synthesized in Example 4 and 50 ml of methanol were added thereto to form a solution. The resulting solution was transferred to a 100 ml-volume autoclave whose atmosphere had been displaced with nitrogen, and the mixture 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 345 mg (yield: 70%) of t-butyl (3S,5S)-6-t-butoxy-3,5-dihydroxyhexanoate. The diastereoselectivity of t-butyl (3S,5S)-6-t-butoxy-3,5-dihydroxyhexanoate was determined in the same manner as in Example 5 and found to be 71 %de.

Provenance & Evidence