Uses
4-Aminotetrahydro-2H-thiopyran 1,1-dioxide, HCl
Synthesis
The general procedure for the synthesis of 4-aminotetrahydro-2H-thiopyran 1,1-dioxide hydrochloride from tert-butyl (1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbamate was as follows: tert-butyl (1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbamate (3.14 g) was dissolved in ethyl acetate (110 mL) that was preheated to 50 °C, to which a solution was subsequently 4M HCl-ethyl acetate solution (30 mL) was added. The reaction mixture was stirred at room temperature for 19 hours. Upon completion of the reaction, the precipitated white crystals were collected by filtration and washed with ethyl acetate. Finally, the product was dried under reduced pressure to afford 4-aminotetrahydro-2H-thiopyran 1,1-dioxide hydrochloride (2.39 g, 100% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 1.93-2.11 (2H, m), 2.23 (2H, d, J=14.4 Hz), 3.08-3.21 (2H, m), 3.21-3.46 (3H, m), 8.10 (3H, br.s.).
References
[1] Patent: EP2261213, 2010, A1. Location in patent: Page/Page column 53
[2] Patent: EP1486490, 2004, A1. Location in patent: Page 45
[3] Patent: WO2008/34860, 2008, A1. Location in patent: Page/Page column 104
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3548 - 3571
[5] Patent: WO2008/145688, 2008, A2. Location in patent: Page/Page column 92
