Electric Literature of 16800-68-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.
General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t. (2S,3?S)-tert-Butyl (1-Acetyl-1?-methyl-2?,3-dioxo-[2,3?-biindolin]-3?-yl)carbamate (3a)Yield: 165 mg (86%); colorless solid; mp 162-163 C; [alpha]D27 -21.4 (c0.5, CHCl3).HPLC: CHIRALPAK IB, n-heptane/EtOH (7:3), 1.0 mL/min, tR (major) =8.5 min, tR (minor) = 11.4 min, lambda = 230 nm; >20:1 dr; 99% ee.IR (ATR): 3307, 2962, 2641, 2322, 2083, 1919, 1902, 1811, 1771, 1709,1602, 1581, 1334, 755, 654 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.55 (m, 2 H, NH, ArH), 7.44 (d, J = 8.0Hz, 1 H, ArH), 7.25 (d, J = 8.0 Hz, 1 H, ArH ), 7.00 (td, J = 8.0, 4.0 Hz, 2 H,ArH), 6.90 (d, J = 8.0 Hz, 1 H, ArH), 6.59 (d, J = 4.0 Hz, 1 H, ArH), 6.51 (t,J = 8.0 Hz, 1 H, ArH), 5.12 (s, 1 H, CH), 3.17 (s, 3 H, NMe), 2.53 (s, 3 H,COCH3), 1.19 [s, 9 H, C(CH3)3].13C NMR (101 MHz, CDCl3): delta = 192.4, 172.8, 171.9, 153.6, 152.5,143.7, 136.4, 129.3, 126.5, 125.5, 124.7, 124.2, 123.6, 121.6, 117.3,108.0, 79.9, 69.4, 64.4, 28.0 (3 C), 26.2, 24.2.MS (ESI): m/z = 458.1 [M + Na]+.HRMS (ESI): m/z [M + Na]+ calcd for C24H25N3O5Na: 458.1686; found:458.1687.
The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.
Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem