HCID 57137252, compound → HCID 57120352, compound

HRID 982190Notes

Reaction equation

[C:1]([O:5][CH2:6][C@@H:7]([OH:19])[CH2:8][C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][CH2:6][C@@H:7]([OH:19])[CH2:8][C@H:9]([OH:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 30 °C

Procedure

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.

Workup

additionwere added
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-bd525961f2974014aca0747a71db3465
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994602

Reaction notes

Loading…