Reaktion #2198702

Reaktionsgleichung

NaN3

3-{2-[2-(2-tosylsulfonyloxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

3-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

→

title compound

3-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

Lösungsmittel

EtOAc

DMF

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Extraktionextracted with EtOAc (4×100 mL)
3. 3
   WaschenThe organic layer was washed with water (100 mL) and brine (100 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   SonstigeThe solvent was removed in vacuo
6. 6
   Sonstigeto give an oil
7. 7
   Sonstigeover 3 days
8. 8
   SonstigeThe catalyst was removed by filtration and solvent
9. 9
   Sonstigeremoved in vacuo

Vorschrift

NaN3 (35 g, 538 mmol) was added to a stirring solution of 3-{2-[2-(2-tosylsulfonyloxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (20 g, 46 mmol) in DMF (150 mL) and the reaction was stirred overnight. Reaction was diluted with water (200 mL) and extracted with EtOAc (4×100 mL). The organic layer was washed with water (100 mL) and brine (100 mL) and dried over Na2SO4. The solvent was removed in vacuo to give an oil. Column chromatography EtOAc/Hex (1:4) gave an oil which corresponds to the 3-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester, (M+1)=304. This oil was hydrogenated using Pd (5% on carbon) in EtOAc under hydrogen (1 atm.) over 3 days. The catalyst was removed by filtration and solvent removed in vacuo to give an oil corresponding to the title compound, (M+1)=278.

Quelle