(4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester → tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate

HRID 1980295Notes

Reaction equation

HRID 1980295 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:4](C(OCC2C=CC=CC=2)=O)[C:3]1=[O:24]>CO.[H][H].[Pd]>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[NH:4][C:3]1=[O:24]

Participants

5

Reactant 1

HCID 13053974(4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester

Product 1

HCID 13053976tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylateYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

8.5 g of tert.-butyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 200 ml of methanol, and 0.1 g of palladium black is added thereto. The mixture is shaken at room temperature in hydrogen gas atmosphere under atmospheric pressure. After the reaction the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue obtained is washed with n-hexane. 5.0 g of tert.-butyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals. Yield: 98.2%

Workup

  1. customAfter the reaction the catalyst
  2. customis removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. washis washed with n-hexane

Sources & evidence

ORD record
ord-2a99e26b85cc4317a8256e0be7222d00
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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