Reacción #52484

Ecuación de reacción

N-[1-(4-bromophenyl)-cyclopropyl]-propionamide

Intermediate 117

N-[1-(4-bromophenyl)-cyclopropyl]-propionamide

NaHCO3

→

title compound

[1-(4-Bromophenyl)-cyclopropyl]-propylamine

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   ExtracciónThis mixture was extracted with EtOAc
3. 3
   Lavadothe combined organic layers were washed with H2O and saturated aqueous NaCl
4. 4
   Secadobefore being dried (MgSO4)
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of N-[1-(4-bromophenyl)-cyclopropyl]-propionamide (Intermediate 117, 85.0 mg, 0.32 mmol) in THF (5 mL) at 0° C. was added BH3-Me2S (48.0 mg, 0.63 mmol; 0.31 mL of a 2M solution in THF). The solution was heated to 55° C. for 17 hours, cooled to room temperature, saturated aqueous NaHCO3 was added and the resulting mixture was stirred for 2 hours. This mixture was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound was isolated by column chromatography (10-30% EtOAc—hexanes).

Fuente