Synthesis
General procedure for the synthesis of tert-butyl (S)-[1-(4-bromophenyl)-ethyl]-carbamate from di-tert-butyl dicarbonate and (S)-1-(4-bromophenyl)ethylamine: At room temperature, di-tert-butyl dicarbonate (0.33 g, 1.5 mmol) was added to a methylene chloride (5 mL) (1.5 mmol) solution of (S)-1-(4-bromophenyl)ethylamine (0.30 g, 1.5 mmol). ) solution and the reaction mixture was stirred overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford the target product tert-butyl (S)-[1-(4-bromophenyl)-ethyl]-carbamate (0.45 g, 1.5 mmol, 100% yield). Mass spectrum (ESI) m/z 300 (M + H)+.
References
[1] Patent: US2015/284375, 2015, A1. Location in patent: Paragraph 0302; 0303
[2] Patent: WO2016/124939, 2016, A1. Location in patent: Paragraph 00337; 00338
[3] Patent: WO2014/4229, 2014, A1. Location in patent: Page/Page column 8
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3176 - 3178
[5] Patent: WO2016/118666, 2016, A1. Location in patent: Paragraph 0417; 0418; 0419