Electric Literature of 1914-02-9,Some common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (141 mg, 0.745 mmol) in DMF(7 mL), was added triethylamine (125 muL, 0.897 mmol) and HATU (322 mg, 0.847 mmol). After stirring atroom temperature for 5 min, 3,3-dimethylindoline (5s, 101 mg, 0.686 mmol) was added and stirringcontinued at room temperature overnight. The mixture was then partitioned between with EtOAc andbrine. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was purified bysilica gel column chromatography to give (R)-tert-butyl (1-(3,3-dimethylindolin-1-yl)-1-oxopropan-2-yl)carbamate (205 mg) as a white solid. LCMS m/z = 319.4 [M+1]+; 1H NMR (400 MHz, CDCl3) delta ppm1.358 (s, 3H), 1.364 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H), 1.45 (s, 9H), 3.78 (d, 1H, J = 10.0 Hz), 4.00 (d, 1H, J =10.0 Hz), 4.54-4.61 (m, 1H), 5.46 (d, 1H, J = 8.5), 7.07-7.10 (m, 1H), 7.15-7.16 (m, 1H), 7.20-7.24 (m, 1H),8.17 (d, J = 8.1 Hz, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,3-Dimethylindoline, its application will become more common.
Reference:
Article; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem