Synthesis
General procedure for the synthesis of 2-aminooxyethanol from 2-(2-hydroxyethoxy)isoindoline-1,3-dione: A mixed solution of the product of Example 13a (15.57 g, 75.2 mmol) and hydrazine hydrate (5.4 mL, 0.11 mol) in methanol (150 mL) was heated to 70 °C and reacted for 1.5 hours. After completion of the reaction, it was cooled to room temperature and chloroform (100 mL) was added to the reaction mixture. The resulting slurry was filtered and washed with chloroform (100 mL x 2). The filtrates were combined and concentrated, and the residue was distilled at 75-80 °C under vacuum at 0.025 mmHg to give the colorless oily product 2-aminooxyethanol (4.54 g, 78% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) δ 3.78 (s, 4H) and 13C NMR (75 MHz, CDCl3) δ 76.3,60.7.
References
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2829 - 2832
[2] Journal of the Chemical Society, Chemical Communications, 1986, # 12, p. 903 - 904
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6367 - 6382
[4] Patent: WO2006/99416, 2006, A1. Location in patent: Page/Page column 84
[5] Patent: JP2016/34901, 2016, A. Location in patent: Paragraph 0039; 0055; 0056
