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

HRID 1702199Notes

Reaction equation

HRID 1702199 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 condensed 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% M.p. 135°-136° C.

Workup

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

Sources & evidence

ORD record
ord-1759ec4a59774265980c3c4c243f74b5
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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