Synthesis
General method: Di-tert-butyl dicarbonate ((Boc)2O, 1.0 mmol) was mixed with monomethylamine (1.0 mmol) and the reaction was carried out with stirring at room temperature for the reaction time as shown in Table 1.The progress of the reaction was monitored by thin layer chromatography (TLC). In most cases, the purity of the resulting Boc-protected tert-butyl methyl-carbamate was satisfactory and no further purification was required. In a few cases, the products needed to be purified by silica gel column chromatography (eluent ratio: ethyl acetate/petroleum ether = 1:2). All products were characterized by infrared spectroscopy (IR), nuclear magnetic resonance hydrogen spectroscopy (1H NMR) and their physical properties.
References
[1] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246
[2] Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4566 - 4575
[3] Letters in Organic Chemistry, 2013, vol. 10, # 2, p. 121 - 125
[4] Patent: WO2008/33567, 2008, A1. Location in patent: Page/Page column 41
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 2, p. 107 - 115
