Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate → methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate

HRID 1181587Notes

Reaction equation

HRID 1181587 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]>CO>[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]

Participants

3

Reactant 1

HCID 86605593Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate

Product 1

HCID 58662605methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionateYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate (330 mg) obtained in Step 2 was dissolved in methanol (10 ml), 5% rhodium-alumina (43 mg) was added, and the mixture was hydrogenated at atmospheric pressure overnight. The reaction mixture was filtered through Celite, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (291 mg).

Workup

  1. customwas hydrogenated at atmospheric pressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9d54567fe5574bd0b853fe09ce4a243e
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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