Sodium Azide → tert-Butyl 12-amino-4,7,10-trioxadodecanoate

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.

1. customReaction
2. extractionextracted with EtOAc (4×100 mL)
3. washThe organic layer was washed with water (100 mL) and brine (100 mL)
4. dry with materialdried over Na2SO4
5. customThe solvent was removed in vacuo
6. customto give an oil
7. customover 3 days
8. customThe catalyst was removed by filtration and solvent
9. customremoved in vacuo

ORD record

ord-1881bffb4dcd4a77967923a929fa6182

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288349B2