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

HRID 335382Notes

Reaction equation

HRID 335382 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13]CS([O-])(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+]=[N-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH2:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86655556HCID 86655556, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 146 g of [2-{2-(t-butoxycarbonylamino)ethoxy}ethyl]methane sulfonate was dissolved in 500 ml DMF, was added 134 g of sodium azide. The reaction mixture was stirred at 70° C. for 20 h, and then concentrated under reduced pressure. The resulting residue was dissolved in 1,200 ml water and extracted with EA. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was dissolved in 2,000 ml THF, to which was added 162 g of triphenylphosphine. The reaction mixture was stirred at RT for 2 h, after which was added 200 ml water. The reaction mixture was stirred at RT for 18 h and concentrated to 500 ml under reduced pressure. Then the resulting precipitate was filtered off. The filtrate was further concentrated under reduced pressure to remove THF, and washed with MC. The aq layer was concentrated to obtain 86.2 g of compd 42 as a liquid. 1H NMR (400 MHz; CDCl3) δ 4.96 (br s, 1H), 3.54-3.48 (m, 4H), 3.34 (q, 2H), 2.88 (t, 2H), 1.48-1.46 (m, 11H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 1,200 ml water
  3. extractionextracted with EA
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in 2,000 ml THF, to which
  7. additionwas added 162 g of triphenylphosphine
  8. stirringThe reaction mixture was stirred at RT for 2 h
  9. additionafter which was added 200 ml water
  10. stirringThe reaction mixture was stirred at RT for 18 h
  11. concentrationconcentrated to 500 ml under reduced pressure
  12. filtrationThen the resulting precipitate was filtered off
  13. concentrationThe filtrate was further concentrated under reduced pressure
  14. customto remove THF
  15. washwashed with MC
  16. concentrationThe aq layer was concentrated

Sources & evidence

ORD record
ord-ebc9536f52ce47209984ec2ec77acc94
Source dataset
uspto-grants-2014_11
Patent number
US08884008B2

Reaction notes

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