HCID 18397496, compound → HCID 15887477, compound

HRID 377201Notes

Reaction equation

HRID 377201 reaction equation
[CH:1]([O:5][C:6]1[CH:7]=[C:8]([C@@:14]2([CH3:20])[O:18][C:17](=[O:19])[NH:16][CH2:15]2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])=[C:2]([CH3:4])[CH3:3]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C@@:14]2([CH3:20])[O:18][C:17](=[O:19])[NH:16][CH2:15]2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 18397496HCID 18397496, compound

Product 1

HCID 15887477HCID 15887477, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

360 mg of (R)-(-)-5-(3-isobutenyloxy-4-methoxyphenyl)-5-methyl-2-oxazolidinone is dissolved in 10 ml of ethyl acetate and mixed with 50 mg of palladium/10% carbon. It is hydrogenated until hydrogen absorption is completed. After filtration on diatomaceous earth and concentration by evaporation in a vacuum, an oily residue is obtained. The crude product is purified by chromatography on a silica gel column, with a hexane-acetone mixture as eluant. 186 mg of (R)-(-)-5-(3-isobutyloxy-4-methoxyphenyl)-5-methyl-2-oxazolidinone, melting point 93.7° C., results. [α]D =-24.7°.

Workup

  1. customIt is hydrogenated until hydrogen absorption
  2. filtrationAfter filtration
  3. concentrationon diatomaceous earth and concentration
  4. customby evaporation in a vacuum
  5. customan oily residue is obtained
  6. customThe crude product is purified by chromatography on a silica gel column, with a hexane-acetone mixture as eluant

Sources & evidence

ORD record
ord-a3d625bc09b7491c95d749b233c59617
Source dataset
uspto-grants-2000_02
Patent number
US06025376

Reaction notes

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