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

HRID 1109666

Reaction equation

HRID 1109666 reaction equation
C1OC1CC.[C:6]1([CH2:12][C@H:13]([N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[C:14](Cl)=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H][H].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.[Pd]>[CH2:12]([C@H:13]([N:17]1[C:21](=[O:22])[C:20]2[C:19](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]1=[O:27])[CH:14]=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 78341,2-EpoxybutaneHCID 656671Sodium PyrosulfiteHCID 105671973-phenyl-2(S)-phthalimidopropionyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 110658013-Phenyl-2(S)-phthalimidopropan-1-alYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1 mol of 1,2-butylene oxide and 23.5 g of Pd/C (5% Pd) were added to a solution of 0.5 mol of 3-phenyl-2(S)-phthalimidopropionyl chloride in 1200 ml of toluene. The suspension was hydrogenated at room temperature and atmospheric pressure while stirring vigorously for 17 hours, whereby 11.3 l of hydrogen were taken up. Thereafter, the suspension was filtered over a filter aid and the residue was washed with toluene. The filtrate and washings were combined and treated while stirring with a solution of 0.5 mol of sodium pyrosulphite in 1 l of water. After stirring at room temperature for 4.5 hours the phases were separated. The aqueous phase was washed with 500 ml of toluene. The toluene phases were washed with 350 ml of water. The combined aqueous phases were treated with 1400 ml of toluene and 420 ml of 3N sulphuric acid and stirred at 60° for 6 hours. Thereafter, the phases were separated and the aqueous phase was extracted with 500 ml of toluene. The toluene phases were washed with water, combined, dried over MgSO4 and evaporated. There were obtained 97.8 g (70%) of (S)-α-benzyl-1,3-dioxo-2-isoindolineacetaldehyde as a white solid, melting point 115°-117°, [α]D20 -200° (1% in ethyl acetate).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThereafter, the suspension was filtered over a filter aid
  3. washthe residue was washed with toluene
  4. additiontreated
  5. stirringAfter stirring at room temperature for 4.5 hours the phases
  6. customwere separated
  7. washThe aqueous phase was washed with 500 ml of toluene
  8. washThe toluene phases were washed with 350 ml of water
  9. additionThe combined aqueous phases were treated with 1400 ml of toluene and 420 ml of 3N sulphuric acid
  10. stirringstirred at 60° for 6 hours
  11. customThereafter, the phases were separated
  12. extractionthe aqueous phase was extracted with 500 ml of toluene
  13. washThe toluene phases were washed with water
  14. dry with materialdried over MgSO4
  15. customevaporated

Sources & evidence

ORD record
ord-6f2ab25ca6a94323992c7ceca80a89bb
Source dataset
uspto-grants-1994_06
Patent number
US05321166

Linked notes

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