With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.
Cuprous iodide (3.6 g, 18 mmol) was added to a mixture of tert-butyl (R)-(2- oxopiperidin-3-yl)carbamate (10 g, 47 mmol), 4-bromo-2-fluoro-l-iodobenzene (14 g, 47 mmol), and potassium phosphate tribasic (15 g, 70 mmol) in dioxane (100 mL), and the mixture was purged with nitrogen for 20 minutes. N^V-dimethylethylenediamine (2.0 mL, 18.7 mmol) was added, and the reaction mixture was stirred at 90 C overnight. The reaction mixture was filtered through celite, washed with ethyl acetate and concentrated in vacuo. The crude product was purified by column chromatography (30% ethyl acetate in pet ether). The mixture was further purified by SFC to give tert- butyl (i?)-(l-(4-bromo- 2-fluorophenyl)-2-oxopiperidin-3-yl)carbamate (3.0 g, 7.8 mmol, 17 % yield) and tert- butyl (i?)-(l-(3-fluoro-4-iodophenyl)-2-oxopiperidin-3-yl)carbamate (1.8 g, 4.1 mmol, 8.8 % yield). Analytical data for Intermediate 2: NMR (300 MHz, CDCh):? ppm 7.30 – 7.37 (m, 2H), 7.10 – 7.18 (m, 1H), 5.46 (s, 1H), 4.27 (m, 1H), 3.53 – 3.68 (m, 2H), 2.54 – 2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.46 (s, 9H) ; 19FNMR: -117, MS(ESI) m/z: (0151) 387.2/389.2 (M+H)+. Analytical data for Intermediate 3: NMR (300 MHz, CDCh-d) ? ppm 7.49 – 7.00 (m, 2H), 6.92 – 7.00 (m, 1H), 5.46 (s, 1H), 4.27 (dt, J=11.71, 6.00Hz, 1H), 3.54 – 3.68 (m, 2H), 2.54 -2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.74(m, 1H), 1.46 (s, 9H) ; 19F NMR: -117, MS(ESI) m/z: 435.0 (M+H)+.
221874-51-7, As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.
Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHIRUDE, Pravin Sudhakar; CHATTOPADHYAY, Amit Kumar; RACHAMREDDY, Chandrasekhar; WURTZ, Nicholas R.; KICK, Ellen K.; (117 pag.)WO2018/227058; (2018); A1;,
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