Analyzing the synthesis route of 156353-01-4

As the paragraph descriping shows that 156353-01-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.156353-01-4,N-Methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

[0240] A flask was charged with N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide 2 (11.7 g, 67.5 mmol) andTHF (350 mL). The resulting mixture was immersed in a cooling bath at -60C, and methylmagnesium bromide (3.0 Min ether, 33.8 mL, 101.4 mmol) was added via syringe over ? 8 min. The temperature of the bath was allowed to rise to0 C over 6h. At that time, the reaction was diluted with water and EtOAc and stirred vigorously for 10 min. The phaseswere separated, and the aqueous layer was extracted with EtOAc. The organic portions were combined, washed withbrine, dried over MgSO4, filtered, and concentrated. The crude residue was subjected to column chromatography (120g silica, 80 mL/min, 0% to 100% EtOAc/hexanes) to give 4-acetyltetrahydro-4H-pyran 3 (7.05 g, 55.0 mmol, 81%). 1HNMR (400 MHz, CDCl3) for 3: delta 3.95 (ddd, J = 11.6, 4.4, 2.8 Hz, 2 H), 3.38 (dt, Jd = 2.8 Hz, Jt = 11.6 Hz, 2 H), 2.50 (m,1 H), 2.12 (s, 3 H), 1.75 (m, 2 H), 1.65 (m, 2 H). LCMS for 3 (conditions D): tR = 0.83 min, m/e = 129.4 (M+H, base)., 156353-01-4

As the paragraph descriping shows that 156353-01-4 is playing an increasingly important role.

Reference£º
Patent; Merck Sharp & Dohme Corp.; ISERLOH, Ulrich; STAMFORD, Andrew, W.; CUMMING, Jared, N.; (63 pag.)EP2485920; (2016); B1;,
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