Cyclopentanone → HCID 22346193, compound

HRID 1293047Notes

Reaction equation

HRID 1293047 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1>[OH-].[OH-].[Pd+2]>[CH:12]1([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8452CyclopentanoneHCID 187201N-BOC-ethylenediamine

Product 1

HCID 22346193HCID 22346193, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

tert-Butyl 2-aminoethylcarbamate (3.0 g, 18.8 mmol) (Preparation 54) was dissolved in cyclopentanone (30 ml). Pearlman's Catalyst (0.1 g) was added and the reaction mixture was stirred under an atmosphere of hydrogen gas (414 kPa, 100 psi) for 48 hours. The catalyst was filtered off through Arbocel (Trade Mark) and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume). The solvent was removed under reduced pressure to give the title compound (1.5 g) as an oil.

Workup

  1. filtrationThe catalyst was filtered off through Arbocel (Trade Mark)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b22e5b68a4f84017b2394b0a8fc8d617
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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