Reacción #567117

Ecuación de reacción

N-[2-benzyloxy-5-(2-iodo-(1R)-1-[(triethylsilyl)oxy]-ethyl)-phenyl}-methanesulfonamide

sodium azide

triphenylphosphine

→

title compound

N-[2-Benzyloxy-5(2-amino-(1R)-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Disolventes

hexamethylphosphoramide

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature the mixture
2. 2
   Lavadowashed with water
3. 3
   Secadodried over Na2SO4
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 200 mL of THF/H2O (10:1)
6. 6
   workup.STIRRINGAfter overnight stirring at room temperature
7. 7
   Otrothe solvents were removed
8. 8
   Otrothe residue was partitioned between ethyl acetate and water
9. 9
   Secadodried over MgSO4
10. 10
    Concentraciónconcentrated
11. 11
    workup.DISSOLUTIONThe residue was redissolved in 100 mL of THF
12. 12
    workup.ADDITIONtetrabutylammonium fluoride (10 mL, 1 M solution in THF) was added
13. 13
    workup.STIRRINGThe reaction was stirred for 2 hours
14. 14
    Otrothe solvent was removed in vacuo
15. 15
    OtroThe residue was purified by column chromatography on silica gel

Procedimiento

A mixture of N-[2-benzyloxy-5-(2-iodo-(1R)-1-[(triethylsilyl)oxy]-ethyl)-phenyl}-methanesulfonamide (EP 0 659 737) (4.48 g, 8 mmol) and sodium azide (0.65 g, 10 mmol) in 100 mL of hexamethylphosphoramide was stirred at 60° C. overnight. After cooling to room temperature the mixture was diluted with diethyl ether, washed with water, dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in 200 mL of THF/H2O (10:1) and triphenylphosphine (2.62 g, 10 mmol) was added. After overnight stirring at room temperature, the solvents were removed and the residue was partitioned between ethyl acetate and water. The organic layers were combined and dried over MgSO4 and concentrated. The residue was redissolved in 100 mL of THF and tetrabutylammonium fluoride (10 mL, 1 M solution in THF) was added. The reaction was stirred for 2 hours then the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel using triethylamine-methanol-methylene chloride (1:1:3) to give the title compound as a white solid; MS (ES) m/z: 337.4 (M++H).

Fuente