With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.548762-66-9,(2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.
To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.2 g, 0.93 mmol) in acetonitrile (6 mL) were added DIPEA (0.5 mL, 2.80 mmol) and dimethyl 4,4′-(bromomethylene)dibenzoate (0.373 g, 1.03 mmol) at room temperature. The reaction mixture was heated at 85 C for 16 h. The volatiles were removed from the reaction mixture under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (24 g, 12 %-17 % ethyl acetate/ petroleum ether) to obtain dimethyl 4,4′-(((2R,5S)-4-(tert-butoxycarbonyl)-2,5-dimethylpiperazin-1-yl) methylene)dibenzoate (140 mg, 30.2 % yield). LCMS: m/z = 497.2 (M+H); retention time 2.52 min [LCMS method: Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM NH4OAc: acetonitrile (95:5); Mobile phase B: 10 mM NH4OAc:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm]., 548762-66-9
548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics