Reaktion #52484

Reaktionsgleichung

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

Intermediate 117

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

NaHCO3

→

title compound

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   ExtraktionThis mixture was extracted with EtOAc
3. 3
   Waschenthe combined organic layers were washed with H2O and saturated aqueous NaCl
4. 4
   Trocknenbefore being dried (MgSO4)
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

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).

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