Tert-butyl (2-(2-azidoethoxy)ethyl)carbamate → tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

HRID 1245978Notes

Reaction equation

HRID 1245978 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-].[H][H]>[Pd].C1(C)C=CC=CC=1>[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 12106197Tert-butyl (2-(2-azidoethoxy)ethyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen purge, 10% palladium on carbon (9.2 g) was added to a solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (92.0 g, 399 mmol) in toluene (900 mL) in a pressure vessel. The vessel was placed under hydrogen pressure (30 psi, 2.0×105 Pa), and for the first 20 minutes, the hydrogen was replaced every five minutes and brought to a pressure of (20 psi, 1.4×105 Pa). The reaction was maintained under hydrogen pressure (20 psi, 1.4×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure to yield 77.4 g of tert-butyl 2-(2-aminoethoxy)ethylcarbamate as a light green oil.

Workup

  1. customUnder a nitrogen purge
  2. temperatureThe reaction was maintained under hydrogen pressure (20 psi, 1.4×105 Pa) overnight
  3. filtrationThe reaction mixture was filtered through a layer of CELITE
  4. filtrationfilter aid
  5. washthe filter cake was washed with ethanol
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-239f4b27f6ea4b78871e3a777d6bcf08
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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