Water → L-Proline, 1-(1-oxo-3-phenylpropyl)-

HRID 1590808Notes

Reaction equation

HRID 1590808 reaction equation
O.C([O:9][C:10](=[O:26])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:25])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1>[Pd].CO>[C:19]1([CH2:18][CH2:17][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][C@H:11]2[C:10]([OH:26])=[O:9])=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 962WaterHCID 45139423N-(3-phenylpropionyl)-L-proline benzyl ester

Product 1

HCID 10354601L-Proline, 1-(1-oxo-3-phenylpropyl)-Yield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd-C (3.00 g) was added to a 1% water-containing methanol solution (200 ml) of N-(3-phenylpropionyl)-L-proline benzyl ester (25.59 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2.5 hours. After the catalyst was filtered off, the filtrate was concentrated to obtain 18.93 g of N-(3-phenylpropionyl)-L-proline.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-45988458c08441e6ac6efc94489c5565
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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