Synthesis
Example 1: Synthesis of 4-(phthalimido)cyclohexanone
4-(Phthalimido)cyclohexanol (146 g) was mixed with ethyl acetate (1000 mL), followed by the addition of sodium bromide (8 g) and 2,2,6,6-tetramethylpiperidin-1-oxyl radical (TEMPO, 0.5 g). A 10% aqueous sodium hypochlorite solution (1000 mL) was added in batches and the pH of the reaction mixture was adjusted to 7-8 using sodium bicarbonate while maintaining the reaction temperature between 5 and 20 °C. Upon completion of the reaction, the aqueous layer was separated, and the organic layer was washed with saturated aqueous sodium chloride (400 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give a white solid product in 95% yield.
References
[1] Patent: WO2010/78250, 2010, A1. Location in patent: Page/Page column 12
[2] Patent: WO2006/3677, 2006, A1. Location in patent: Page/Page column 10; 16
[3] Patent: US2011/280808, 2011, A1. Location in patent: Page/Page column 62
[4] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
[5] Patent: US2003/100596, 2003, A1
