Application of 177906-48-8, A common heterocyclic compound, 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, molecular formula is C11H22N2O2, its 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.
To a solution of tert-butyl ((lr,4r)-4-aminocyclohexyl)carbamate (1 g, 4.66 mmol) and 1 -fluoro-2-nitrobenzene (commercially available from Sigma- Aldrich, Milwaukee, WI) (0.658 g, 4.66 mmol) in DMF (5 mL) was added K2C03 (1.28 g, 9.32 mmol) at ambient temperature. The resulting reaction mixture was stirred for 12 hours at 60C. After completion of reaction (monitored by TLC (TLC eluent: 30 % EtOAc in petroleum ether)), the reaction mixture was cooled to ambient temperature and water was added to obtain a yellow precipitate. After stirring for 10 minutes, the mixture was filtered and washed with water and then dried under vacuum to afford tert-butyl ((lr,4r)-4-((2-nitrophenyl)amino)cyclohexyl)carbamate as a yellow solid (1.5 g, 95.84 %). lB NMR (300 MHz, DMSO-d6) delta 8.03 (d, J= 8.6 Hz, 1H), 7.87 (d, J= 7.6 Hz, 1H), 7.52-7.43 (m, 1H), 7.1 1 (d, J= 8.7 Hz, 1H), 6.83 (d, J= 7.6 Hz, 1H), 6.71 – 6.57 (m, 1H), 3.42 (m, 1H), 1.99 (s, 2H), 1.81 (s, 2H), 1.45 – 1.20 (m, 2H+2H+1H+9H=14H). m/z (ESI) 336.3 (M+H)+.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics