Tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate → tert-butyl N-(2-(2-aminoethoxy)ethyl)-N-methylcarbamate

HRID 1840837Notes

Reaction equation

HRID 1840837 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]([CH3:17])[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][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 1

HCID 21093756Tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate

Product 1

HCID 85823338tert-butyl N-(2-(2-aminoethoxy)ethyl)-N-methylcarbamateYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate (41.9 g, 170 mmol) in 600 mL of MeOH was treated with 2.5 g of 10% Pd on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 37.2 g of crude tert-butyl 2-(2-aminoethoxy)ethyl(methyl)carbamate as a light yellow liquid.

Workup

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

Sources & evidence

ORD record
ord-6dab2257afa242cda26745ab50f6f3b5
Source dataset
uspto-grants-2004_01
Patent number
US06683088B2

Reaction notes

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