HCID 54348341, compound → HCID 10261413, compound

HRID 1975510Notes

Reaction equation

HRID 1975510 reaction equation
[OH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4](=[O:9])[CH2:5][C:6]([OH:8])=[O:7]>CO.C(O)C.C(O)(C)C.C(O)(C)(C)C.[Ru]>[OH:9][C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:10][OH:11])[CH2:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 1

HCID 54348341HCID 54348341, compound

Product 1

HCID 10261413HCID 10261413, compound

Reagents, catalysts & solvents 5

HCID 23950RutheniumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6386tert-ButanolSolvent

Procedure

That is, the (S)-5,6-dihydroxy-3-oxohexanoic acid derivative shown by formula (2) is dissolved in an alcohol such as methanol, ethanol, iso-propanol, tert-butyl alcohol, etc., the ruthenium-optically active phosphine complex shown by formula (3) is added to the solution in an amount of from 0.0001 to 0.002 mol, and preferably from 0.0001 to 0.001 mol, per mol of the compound of formula (2), the hydrogenation is carried out under a hydrogen pressure of from 10 to 120 kg/cm2, and preferably from 20 to 50 kg/cm2 and at a reaction temperature of from 25° to 100° C., and preferably from 30° to 50° C. The solvent was removed by distillation, and the residue formed is purified by silica gel column chromatography to provide the desired (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative shown by formula (1).

Workup

  1. additionis added to the solution in an amount of from 0.0001 to 0.002 mol
  2. customof from 25° to 100° C.
  3. custompreferably from 30° to 50° C
  4. customThe solvent was removed by distillation
  5. customthe residue formed
  6. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d229cef18cda4679a8b0d875610ea4b9
Source dataset
uspto-grants-1994_02
Patent number
US05286883

Reaction notes

Loading…