Application of 16066-84-5,Some common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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.
General procedure: JohnPhos (22 mg, 0.075 mmol), NaO’Bu (54 mg, 0.564 mmol), Pd2(dba)3(69 mg, 0.075 mmol), and then pyrrolidin-3-ol (49 mg, 0.564 mmol) were added to a solution of Compound 4 (200 mg, 0.376 mmol) and dioxane (5 mL). The mixture was degassed with vacuum/N2 cycles (3chi), stirred at 100 C overnight, filtered, and then concentrated. The residue was purified by RP-HPLC (H20 (100 mM H4HC03)/ACN) to give Compound 6 (58 mg, 29%) as a white solid. 1H NMR (400 MHz, DMSO-i): delta 8.13 (d, 1H), 7.39-7.75 (m, 6H), 7.31 (d, 2H), 7.07 (d, 1H), 6.95-6.99 (m, 1H), 6.72 (s, 1H), 5.08 (d, 1H), 5.02 (d, 1H), 4.79 (d, 1H), 4.43 (d, 1H), 3.80 (s, 3H), 3.47-3.55 (m, 1H), 3.43 (d, 2H), 3.21-3.25 (m, 1H), 2.18 (s, 3H), 1.95-2.10 (m, 1H), 1.90-2.10 (m, 1H), 1.73-1.85 (m, 2H), 0.80 (s, 9H); MS: 538.4 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl methylcarbamate, its application will become more common.
Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (167 pag.)WO2018/170167; (2018); A1;,
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