Synthesis
To a solution of oxetan-3-ol (5 g, 67.5 mmol) and triethylamine (14.11 mL, 101 mmol) in dichloromethane (150 mL) was added methanesulfonyl chloride (6.79 mL, 88 mmol) dropwise at 0 °C. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solid was removed by filtration and the filtrate was washed sequentially with ice water and saturated saline. The organic phase was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure to afford oxetan-3-yl methanesulfonate (11.7 g, 67.5 mmol, 100% yield) as an oil containing 12.2 wt% dichloromethane. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.06 (s, 3H), 4.79-4.82 (m, 2H), 4.86-4.90 (m, 2H), 5.52-5.49 (m, 1H).
References
[1] Patent: WO2013/55910, 2013, A1. Location in patent: Page/Page column 124; 125
[2] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 98; 99
[3] Patent: WO2015/181186, 2015, A1. Location in patent: Page/Page column 169
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9769 - 9789
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2518 - 2532
