1,2-Epoxybutane → 3-Phenyl-2(S)-phthalimidopropan-1-al

HRID 1604747Notes

Reaction equation

HRID 1604747 reaction equation
[C:1]1([CH2:7][C@H:8]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1OC1CC>C1(C)C=CC=CC=1.[Pd]>[C:1]1([CH2:7][C@H:8]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:9]=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 78341,2-EpoxybutaneHCID 105671973-phenyl-2(S)-phthalimidopropionyl chloride

Product 1

HCID 110658013-Phenyl-2(S)-phthalimidopropan-1-al

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

The solution containing the 3-phenyl-2(S)-phthal-imidopropionyl chloride was diluted with 500 ml of toluene and combined with 72.11 g of 1,2-butylene oxide. 23.5 g of palladium on carbon (5%) and 100 ml of toluene were added to the solution. The suspension was hydrogenated for 17 hours with stirring and then filtered and the residue washed with 200 ml of toluene, wherein 3-phenyl-2(S)-phthalimidopropan-1-al was obtained.

Workup

  1. filtrationfiltered
  2. washthe residue washed with 200 ml of toluene

Sources & evidence

ORD record
ord-48d3e33722a84601ad0fa0268b32d2cf
Source dataset
uspto-grants-1999_11
Patent number
US05994555

Reaction notes

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