Reacción #67300

Ecuación de reacción

dimethylsulfide

n-BuLi

N-benzyl-N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine

NH4Cl

→

title compound

Rendimiento 51.3%

N-BENZYL-N-{[(2S)-8-FLUORO-7-(METHYLTHIO)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}ETHANAMINE

Rendimiento 51.3%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas then warmed to room temperature
2. 2
   Extracciónthe solution was extracted with EtOAc
3. 3
   LavadoThe combined organic phases were washed with Na2SO3 (15%), brine
4. 4
   Secadodried (Na2SO4)
5. 5
   Otroevaporated to dryness

Procedimiento

A mixture of N-benzyl-N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine (2.2 g, 7.3 mmol) and 2,2-tetramethylpiperidine (2.5 ml, 14.6 mmol) was added dropwise to n-BuLi (10 ml, 25 mmol) in THF (dry, 10 ml) under N2 at −75° C., followed by the addition of dimethylsulfide (1.32 ml, 14.6 mmol) in THF (dry, 10 ml). The mixture was stirred for 30 min at −75° C., and was then warmed to room temperature. NH4Cl (sat.) was added and the solution was extracted with EtOAc. The combined organic phases were washed with Na2SO3 (15%), brine, dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.3 g). MS m/z (rel. intensity, 70 eV) 347 (2), 149 (12), 148 (100), 92 (7), 91 (92).

Fuente