Reaktion #422564

Reaktionsgleichung

[2-{2-(t-butoxycarbonylamino)ethoxy}ethyl]methane sulfonate

sodium azide

→

42

2-{2-(t-butoxycarbonylamino)ethoxy}ethylamine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in 1,200 ml water
3. 3
   Extraktionextracted with EA
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in 2,000 ml THF, to which
7. 7
   workup.ADDITIONwas added 162 g of triphenylphosphine
8. 8
   workup.STIRRINGThe reaction mixture was stirred at RT for 2 h
9. 9
   workup.ADDITIONafter which was added 200 ml water
10. 10
    workup.STIRRINGThe reaction mixture was stirred at RT for 18 h
11. 11
    Einengenconcentrated to 500 ml under reduced pressure
12. 12
    FiltrationThen the resulting precipitate was filtered off
13. 13
    EinengenThe filtrate was further concentrated under reduced pressure
14. 14
    Sonstigeto remove THF
15. 15
    Waschenwashed with MC
16. 16
    EinengenThe aq layer was concentrated

Vorschrift

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).

Quelle