With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.
125552-89-8, Example 70(IS, 2R) and (1R, 2S)-2-(4-chlorophenyl)-l’-((tetrahydro-2H-pyran-4-yl)methyl) spiro [cyclopropane- 1 ,3′-indolin] -2′-oneRacemic (IS, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin] -2′-one and (1R, 2S)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin] -2′-one (270 mg, 1.0 mmol, 1.0 equiv.) were added to a stirred solution of sodium hydride (60 %, 60 mg, 1.5 mmol) in 5 mL of DMF under argon atmosphere at 0C. After stirring for 1 hour, 4-bromomethyl- tetrahydropyran (215 mg, 1.2 mmol) was added. The reaction mixture was stirred for 14 hours at room temperature. The crude product was purified by HPLC to give the title compound as a white solid (258 mg, 70 %). LC/MS m/e calcd. for C22H22CINO2: 367, observed (M+H)+: 368.2 ? NMR (400 MHz, MeOD-d4) 5ppm 1.39 – 1.55 (m, 2 H) 1.65 (dd, J=13.14, 1.77 Hz, 2 H) 2.11 – 2.25 (m, 3 H) 3.22 (t, J=8.46 Hz, 1 H) 3.37 – 3.47 (m, 2 H)3.79 (d, J=7.33 Hz, 2 H) 3.94 – 4.04 (m, 2 H) 6.09 (d, J=7.58 Hz,l H) 6.76 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.17 – 7.25 (m, 3 H) 7.33 (d, J=8.34 Hz, 2 H). MS calcd. For C22H22CINO2 367, obsd. (ESF) [(M+H)+] 368.
125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HE, Yun; HUANG, Mengwei; YUN, Hongying; WO2011/70039; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics