Methyl Acetate → HCID 57144588, compound

HRID 982191Notes

Reaction equation

[C:1]([O:5][CH2:6][C@@H:7]([OH:16])[CH2:8][C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])([CH3:4])([CH3:3])[CH3:2].C(OC)(=O)C.CCN(CC)CC>CO>[C:1]([O:5][CH2:6][C@@H:7]([OH:16])[CH2:8][C@@H:9]([OH:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 30 °C

Procedure

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.

Workup

customto form a solution
customThe solvent was removed by distillation
customthe residue was purified by silica gel column chromatography (diethyl ether/hexane: 5/1 by volume)

Sources & evidence

ORD record: ord-be3386bcb3d6420da22d450754d6c378
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994602

Reaction notes

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