Reference of 15963-40-3, These common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, its 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.
3.1.57b (24 g, 190.4 mmol, 1.0 equiv) was dissolved in THE and cooled to -15 C. BH3.Me2S (14.4 g, 190.4 mmol, 1.0 equiv) was added drop wise and the reaction mixture was stirred at room temperature for 4 hours. Cooled the reaction mixture at -15 C, NaOH (3M) (25 mL), H202 (50%) (12.9 g, 190.4 mmol, 1.0 equiv) were added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sodium bisulphate and extracted with EtOAc. The organic layer was washed with brine,dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (70 % EtOAc in Hexane) to afford product 3.1.57c (18.7 g, 68 % yield). 1H NMR (400 MHz, DMSO) 64.54 (d, J = 29.8 Hz, 1H), 3.62-3.55 (m, 3H), 3.41 (d, J = 6.5 Hz, 1H), 3.30 (d, J = 6.0 Hz, 1H), 3.13-2.95 (m, 1H), 2.37-2.27 (m, 1H), 2.15 (ddt, J= 8.7, 7.8, 6.2 Hz, 2H), 1.98- 1.84(m, 2H).
The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
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