N-Benzyloxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide → n-Hydroxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727526Notes

Reaction equation

HRID 727526 reaction equation
[H][H].C([O:10][NH:11][C:12](=[O:33])[CH:13]([CH3:32])[C:14]1([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]1=[O:27])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[OH:10][NH:11][C:12](=[O:33])[CH:13]([CH3:32])[C:14]1([CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]1=[O:27]

Participants

5

Reactant 2

HCID 19705438N-Benzyloxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 15887253n-Hydroxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamideYield 89%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

An atmosphere of hydrogen is placed over a mixture of N-benzyloxy-α-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (80.0 mg, 0.189 mmol), MeOH (4.5 mL) and Pearlman's catalyst (15 mg). The mixture is stirred at room temperature for 4 hours. The mixture is filtered, the solids rinsed with MeOH (4×5 mL), and the filtrate concentrated to give 55.9 mg of an oil. Crystallization from hexane provided 46.9 mg (75%) of the title compound as a white solid (mp 107°-108° C.).

Workup

  1. filtrationThe mixture is filtered
  2. washthe solids rinsed with MeOH (4×5 mL)
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-821305881bdd4947904a49a8b4235bba
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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