Some common heterocyclic compound, 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, molecular formula is C6H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: nitriles-buliding-blocks
To a 50 mL round-bottom flask containing 3-cyclopropyl-3-oxopropanenitrile 201 (1.63 g, 14.94 mmol, 1.0 equiv.), ethanol (20 mL), and TEA ( 1.51 g, 14.92 mmol, 1 .0 equiv.), N- hydroxybicyclo[2.2.2]oct-l-carbonimidoyl chloride 20h (2.8 g, 14.92 mmol, 1.0 equiv.) was added. The reaction mixture was stirred for 5 rain at 0 C and then for 2 h at RT. The resulting mixture was diluted with EtOAc (300 mL), washed with brine ( 100 mL x 2), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by Flash-Prep-HPLC using the following conditions: Column, silica gel; mobile phase, PE:EtOAc = 100:0 increasing to PE_EtOAc=80:20 within 30 min; Detector, UV 254 ran. Removal of solvents provided 3-[bicyclo[2.2.2]octan-l -yl]-5-cyclopropyl-l,2-oxazole-4-carbonitrile 20j (1.7 g, 47%) as a light yellow oil.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118431-88-2, its application will become more common.
Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
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