Reference of 88744-04-1,Some common heterocyclic compound, 88744-04-1, name is 9-Fluorenylmethyl Pentafluorophenyl Carbonate, molecular formula is C21H11F5O3, 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.
Example 9; Synthesis of Compound 16 of Example 1; Acid 12 (46 mg, 0.12 mmol) was dissolved in MeOH (4 mL) and hydrogenated for 20 min. using 20% wt Pd/C. The solution was filtered and the solvent was evaporated in vacuo. The solid residue was dissolved in aqueous acetone (3 mL, 1:1) and treated with 9-fluorenylmethyl pentafluorophenyl carbonate (91 mg, 0.24 mmol) and sodium bicarbonate (31 mg, 0.37 mmol) for 4 hours at room temperature. Water (10 mL) was added and the aqueous layer was extracted with ethyl acetate (6×10 mL). Finally, the solvent was dried (Na2SO4) and concentrated. The crude product was purified by flash column chromatography (methanol:ethyl acteate, 1:1) to afford compound 16 (45 mg, 63%).1H NMR (300 MHz, CD3OD, r.t., TMS): delta=1.43 (s, 9H), 2.98-3.13 (m, 2H, H-6+H-8a), 3.18 (m, 1H, H-7), 3.22-3.44 (m, 2H, H-3, H-5), 3.62-3.80 (m, 2H, H-4, H-8b), 4.23 (t, 1H, J=6.8 Hz), 4.32-4.48 (m, 3H), 7.28-7.87 (m, 8H). 13C NMR (100 MHz, CDCl3, r.t.): delta=28.88, 43.42, 48.54, 56.37, 67.78, 72.04, 73.14, 79.03, 80.38, 80.76, 82.97, 120.94-128.78 (aromatic carbons), 142.61-145.43 (aromatic carbons), 157.71, 159.12, 169.46. MS (ES, [M-H]-); Anal. Calcd for C28H33N2O10: 557.21, Found: 557.09. HRMS (ES, [M-H]-); Anal. Calcd for C28H33N2O10: 557.2135, Found: 581.2133.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 9-Fluorenylmethyl Pentafluorophenyl Carbonate, its application will become more common.
Reference:
Patent; UNIVERSITY OF MANITOBA; US2008/275213; (2008); A1;,
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