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

HRID 32372Notes

Reaction equation

HRID 32372 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-]>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

4

Reactant 1

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

Product 1

HCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamateYield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (47.0 g, 0.204 mol) in MeOH was treated with 4 g of 10% Pd on carbon and shaken under H2 (3 Kg/cm2) for 24 hours. The solution was then filtered through a Celite pad and concentrated to give 35.3 g of crude tert-butyl 2-(2-aminoethoxy)ethylcarbamate as a colorless liquid that was used without further purification.

Workup

  1. filtrationThe solution was then filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ea2536f75c7f47378c1824a1c94645c3
Source dataset
uspto-grants-2008_09
Patent number
US07427629B2

Reaction notes

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