benzyl 5-formyl-2(S)-phthalimidopentanoate → 5-Formyl-2(S)-phthalimidopentanoic acid

HRID 543210Notes

Reaction equation

HRID 543210 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][C@H:6]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])[C:7]([O:9]CC1C=CC=CC=1)=[O:8])=[O:2]>C(OCC)(=O)C.[H][H].[Pd]>[CH:1]([CH2:3][CH2:4][CH2:5][C@H:6]([N:17]1[C:18](=[O:27])[C:19]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]2[C:21]1=[O:22])[C:7]([OH:9])=[O:8])=[O:2]

Participants

5

Reactant 1

HCID 11003033benzyl 5-formyl-2(S)-phthalimidopentanoate

Product 1

HCID 132416335-Formyl-2(S)-phthalimidopentanoic acidYield 102.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

Benzyl 5-formyl-2(S)-phthalimidopentanoate (4.72 g) was dissolved in 230 ml of ethyl acetate and hydrogenated at 5 psig of hydrogen over 0.82 g of 10% palladium on carbon. After the uptake of 1 equivalent of hydrogen, catalyst was removed by filtration. Removal of solvent afforded 3.64 g of 5-formyl-2(S)-phthalimidopentanoic acid.

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-109af7cb014a4d95869f30019591696c
Source dataset
uspto-grants-1987_04
Patent number
US04661479

Reaction notes

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