N-Boc-N-propyl-O-allylhydroxylamine → N-Boc-N-propyl-N-propoxyamine

HRID 496776Notes

Reaction equation

HRID 496776 reaction equation
[C:1]([N:8]([CH2:13][CH2:14][CH3:15])[O:9][CH2:10][CH:11]=[CH2:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CCOC(C)=O.[Pd]>[C:1]([N:8]([CH2:13][CH2:14][CH3:15])[O:9][CH2:10][CH2:11][CH3:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 1

HCID 22322817N-Boc-N-propyl-O-allylhydroxylamine

Product 1

HCID 22322626N-Boc-N-propyl-N-propoxyamineYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Boc-N-propyl-O-allylhydroxylamine (6.0 g) was dissolved in EtOAc (100 mL). 10% Palladium-on-carbon (0.5 g) was added, and the mixture was purged with nitrogen. The nitrogen line was exchanged for a balloon of hydrogen, and the mixture was stirred at room temperature for 6 hours. The catalyst was removed by filtration through a pad of Celite and the solvents were removed in vacuo to give a yellow oil which was purified by flash chromatography on silica gel eluting with 5% EtOAc/hexanes to give the title compound as a colorless oil (5.8 g).

Workup

  1. customthe mixture was purged with nitrogen
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. customthe solvents were removed in vacuo
  4. customto give a yellow oil which
  5. customwas purified by flash chromatography on silica gel eluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-e02c7a05031c4e2f9ace01c843266982
Source dataset
uspto-grants-2005_09
Patent number
US06946481B1

Reaction notes

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