With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.
To a solution of tert-butyl cis-3,5-dimethylpiperazine-1-carboxylate (Combi-Blocks Inc., San Diego, Calif., USA, 130 g, 580 mmol, 1.0 equiv) and triethylamine (100 mL, 700 mmol, 1.2 equiv) in tetrahydrofuran (1250 mL, 10 mL/g) was added acryloyl chloride (56 mL, 700 mmol, 1.2 equiv) at 0 C. The reaction mixture was stirred for 1 h at 0 C. The reaction mixture was diluted with ethyl acetate (2.0 L) and washed with water (2*500 mL). The organic layer was washed with 1 N aqueous HCl (500 mL), saturated NaHCO3 (500 mL), and brine (500 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed to a plug of silica gel and purified by silica gel column chromatography (30-40% EtOAc/hexane) to provide the title compound as off-white solid (140 g, 91%). MS (ESI, +ve ion) m/z: 269.0 [M+1]; 1H NMR (400 MHz, DMSO-d6) delta 6.78-6.72 (ddd, J=16.7, 10.4, 1.5 Hz, 1H), 6.15-6.11 (dt, J=16.6, 1.9 Hz, 1H), 5.70-5.67 (dt, J=10.6, 1.9 Hz, 1H), 4.35-4.25 (m, 2H), 3.82 (d, J=12.5 Hz, 2H), 3.01-2.95 (m, 2H), 1.43-1.42 (d, J=1.6 Hz, 9H), 1.19-1.14 (m, 6H).
129779-30-2, 129779-30-2 (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 10822535, apiperazines compound, is more and more widely used in various fields.
Reference£º
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics