Acetic Acid → HCID 44241966, compound

Participants

Reaction Steps

A solution of (R)-2-(1H-Indol-3-yl)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (400 mg, 1.65 mmol) and 4-dimethylamino-4-phenylcyclohexanone (358.7 g, 1.65 mmol) in anhydrous tetrahydrofuran (50 mL) was mixed with sodium sulphate (1.1 g) and stirred for 2 h at room temperature. After adding acetic acid (248 mg, 4.1 mmol) sodium triacetoxyboron hydride (524 mg, 2.47 mmol) was added and the reaction mixture stirred for 16 h at room temperature. The solvent was removed in a vacuum, the residue mixed with 1M potassium carbonate solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography (400 g, 20×5.6 cm) with ethyl acetate/isopropanol/triethylamine (10:0.3:0.01→5:1:0.1).

Provenance & Evidence