Reacción #312570

Ecuación de reacción

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine

2-methoxy-ethanesulfonyl chloride

→

2-Methoxy-ethanesulfonic acid [3-(2-benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenyl]-amide

Disolventes

toluene

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   Lavadowashed with saturated aqueous NaHCO3 solution (100 mL)
4. 4
   ExtracciónThe aqueous layer was extracted with CH2Cl2 (2×50 ml)
5. 5
   Concentraciónthe organic layer was concentrated to an oil
6. 6
   workup.DISSOLUTIONThis was dissolved in EtOAc which
7. 7
   Otroto separate
8. 8
   OtroThe EtOAc layer was separated
9. 9
   Lavadowashed with saturated aqueous NaHCO3 solution (100 mL)
10. 10
    ExtracciónThe aqueous layer was extracted with EtOAc (2×50 ml)
11. 11
    Lavadothe combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
12. 12
    Secadodried over Na2SO4
13. 13
    Filtraciónfiltered
14. 14
    Concentraciónconcentrated to a crude orange liquid (3.77 g, ˜100%)

Procedimiento

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine (2.71 g, 8.84 mmol) stirred in pyridine (25 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (2.1 g, 13.26 mmol) dropwise causing a color change from yellow to bright orange. The reaction was allowed to warm to room temperature gradually and stirred 18 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with CH2Cl2 (2×50 ml) and the organic layer was concentrated to an oil. This was dissolved in EtOAc which caused an oil to separate. The EtOAc layer was separated and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with EtOAc (2×50 ml) and the combined organic layer was washed with saturated aqueous NaCl solution (50 ml), dried over Na2SO4, filtered and concentrated to a crude orange liquid (3.77 g, ˜100%). (TLC 75% EtOAc/hexanes Rf 0.48);

Fuente