Synthesis
General procedure for the synthesis of 2-(4-hydroxycyclohexyl)isoindole-1,3-dione from N-ethoxycarbonylphthalimide and 4-aminocyclohexanol: 4-aminocyclohexanol (2.627 g, 22.81 mmol) and 1,3-dioxo-1,3-dihydroisoindole-2-carboxylic acid ethyl ester (5 g, 22.81 mmol) were placed in large test tubes using a heat gun until both were completely melted and continued heating for 5 minutes. After completion of the reaction, the resulting solution was allowed to cool to room temperature and a solid was formed. The solid product was transferred to a flask, dissolved in dichloromethane (CH2Cl2) and purified by column chromatography (75% ethyl acetate/hexane) to afford 4.57 g of 2-(4-hydroxycyclohexyl)isoindole-1,3-dione in 81% yield.LCMS (m/z): [M+H+MeCN]+ = 287.1.
References
[1] Patent: US2008/269193, 2008, A1. Location in patent: Page/Page column 33
[2] Patent: WO2013/13188, 2013, A1. Location in patent: Paragraph 00486
[3] Patent: US9416132, 2016, B2. Location in patent: Page/Page column 183; 184
[4] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
