Water → HCID 58101298, compound

Participants

Reaction Steps

60% Sodium hydride suspension in mineral oil (0.412 g, 10.3 mmol) in dry dimethylformamide (25 mL) was stirred at room temperature under an atmosphere of nitrogen. tert-Butyl 1-[1-(4-chlorophenyl)cyclobutyl]-1,3,4,9-tetrahydro-2H-b-carboline-2-carboxylate (3.0 g, 6.87 mmol) was added in small portions. After 30 min stirring at room temperature 2-bromoacetonitrile (1.235 g, 10.3 mmol) in dimethylformamide (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for two days. Water was added (1 mL). The reaction mixture was concentrated in vacuo, dichloromethane (100 mL) was added and the organic solution successively washed with water (50 mL), saturated NaHCO3 solution (30 mL) and water (30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane). Yield: 2.7 g (83%).

Provenance & Evidence