Toluene → tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

HRID 1920269Notes

Reaction equation

HRID 1920269 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N+]=[N-].C1(C)C=CC=CC=1>CO.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 2

HCID 1140TolueneHCID 12106197Tert-butyl (2-(2-azidoethoxy)ethyl)carbamate

Product 1

HCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (52 g, 226 mmol) in methanol (500 mL) was added to a Parr vessel containing 10% palladium on carbon (4 g) which had been wetted with toluene (30 mL). The mixture was placed under hydrogen pressure (30 psi; 2.0×105 Pa). After 18.5 hours analysis by thin layer chromatography indicated that the reaction was not complete. Catalyst (0.5 g) was added and the hydrogenation was continued for an additional 4 hours. The reaction mixture was filtered through a layer of CELITE filter aid and a glass wool filter pad. The filter cake was rinsed with a mixture of isopropanol and methanol. The filtrate was concentrated under reduced pressure to provide tert-butyl 2-(2-aminoethoxy)ethylcarbamate.

Workup

  1. waitthe hydrogenation was continued for an additional 4 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. filtrationa glass wool filter pad
  5. washThe filter cake was rinsed with a mixture of isopropanol and methanol
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b74a20833f51496f9551a202d442f4bc
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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