(S)-3-((R)-6-(4-Fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one → (S)-3-((R)-6-(4-Fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hexanoyl)-4-isopropyloxazolidin-2-one

HRID 1361061Notes

Reaction equation

HRID 1361061 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][CH2:8][CH:9]=[CH:10][CH2:11][C@@H:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=2)[C:13]([N:15]2[C@@H:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][O:17][C:16]2=[O:23])=[O:14])=[CH:4][C:3]=1[CH3:35]>C1C=CC=CC=1>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=2)[C:13]([N:15]2[C@@H:19]([CH:20]([CH3:21])[CH3:22])[CH2:18][O:17][C:16]2=[O:23])=[O:14])=[CH:4][C:3]=1[CH3:35]

Participants

3

Reactant 1

HCID 66968246(S)-3-((R)-6-(4-Fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one

Product 1

HCID 59775183(S)-3-((R)-6-(4-Fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hexanoyl)-4-isopropyloxazolidin-2-oneYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(S)-3-((R)-6-(4-fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one (430 mg, 0.88 mmol) was dissolved into 4 mL benzene and to it added Wilkinson catalysis (81.0 mg, 0.088 mmol). The solution was saturated with H2 (stream of H2 bubbled through solution) and then stirred for 8 h at room temperature under an atmosphere of hydrogen balloon. The solvent was removed under reduced pressure and the product isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give 418 mg of the title compound as a colorless oil.

Workup

  1. additionadded Wilkinson catalysis (81.0 mg, 0.088 mmol)
  2. customThe solvent was removed under reduced pressure
  3. customthe product isolated by flash column chromatography
  4. washeluting with 0% to 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fbe82b7f061c41bf8f03c4dff9740719
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

Loading…