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

Participants

Reaction Steps

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.

Provenance & Evidence