HCID 67171742, compound → 1-{[2-(Trimethylsilyl)ethoxy]methyl}piperazin-2-one

HRID 545216Notes

Reaction equation

HRID 545216 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:13](=[O:25])[CH2:12]1)=O)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH3:22][Si:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][O:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][C:13]1=[O:25]

Participants

5

Reactant 1

HCID 67171742HCID 67171742, compound

Product 1

HCID 671697051-{[2-(Trimethylsilyl)ethoxy]methyl}piperazin-2-one

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Oxo-4-(2-trimethylsilanyl-ethoxymethyl)-piperazine-1-carboxylic acid benzyl ester (3.00 g, 8.22 mmol) was dissolved in THF (30 ml) and MeOH (30 ml), and vigorously stirred on 20% Pd(OH)2/C under a hydrogen atmosphere (1 atm) for 14 h. After N2 was purged, Pd(OH)2/C was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH=95/5 to 90/10) to obtain the intended compound as a colorless oil.

Workup

  1. customAfter N2 was purged
  2. customPd(OH)2/C was removed through filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH=95/5 to 90/10)

Sources & evidence

ORD record
ord-5a54ade3734c4421975d50572c9a3e62
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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