Synthetic Route of 3637-61-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3637-61-4, name is Cyclopentanemethanol. A new synthetic method of this compound is introduced below.
To a suspension of Nail (98 rng, 2.5 mmol, 5 eq) in THF (5 mL) at 0C cyclopentanernethanol (263 iL, 2.5 mrnol, 5 eq) was added. The reaction was stirred at 0C for 30 mm and 6-(6-bromopyridin-2-yl)-3 -[(2-chloro-4-fluorophenyl)sulfanyl]- 6-(thiophen-3-yI)piperidine-2,4-dione (250 mg, 0.49 mmol, I eq) was added. The reaction was then stirred overnight under reflux and quenched by the addition of water (10 mL) and HCI 1M (5 mL). The aqueous phase was extracted with ethyl acetate (3 x 15 mL) and the combined organic phases were dried with Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluent: heptane/ ethyl acetate: 75/25) to give 3- [(2-chloro-4-fluorophenyl)sulfanyl]-6-[6-(cyclopentylmethoxy)pyridin-2-yl] -6- (thiophen-3-yl)piperidine-2,4-dione (192 mg, 0.36 mmol) in 74 % yield.?H NMR (MeOD-d4, 400 MHz): 6 7.71 (dd, .1 8.0, 7.6 Hz, 1H), 7.44 (dd, J 8.8, 7.2 Hz, I H), 7.27 (dd, .1 = 2.8, 1 .2 Hz, 1 H), 7.1 5-7.1 1 (m, 2H), 7.09 (dd, J 4.8, 2.8 Hz. 11-1), 6.75 (d,.J= 8.4 Hz, IH), 6.54 (td,.J= 8.4, 2.8 Hz, IH), 5.99 (dd,J= 8.8, 6.0 Flz, IF). 4.27-4.18 (rn, 21-1). 3.87 (d,.J= 16.4 l-lz, IH), 3.45 (d,.1 16.4 Hz, 1H), 2.36-2.28 (111, 11-1), l.83-l.74(rn, 2H), 1.66-1.53 (m, 4H), 1.39-1.29 (m, 2H).?3C NMR (MeOD-d4, 100 MHz): 6 166.9, 161.6, 158.6 (d,J 245 Hz), 157.2, 143.5, 138.2, 130.7 (d, J= 4 Hz), 124.8 (d, J 8.5 Hz), 124.7, 124.5, 120.1, 114.7 (d, J= 25 Hz), 112.3 (d, .J= 21 Hz), 111.8, 108.0, 100.0, 68.3, 59.3, 39.1, 37.3, 27.5,23.4.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,3637-61-4, Cyclopentanemethanol, and friends who are interested can also refer to it.
Reference:
Patent; SPERMATECH AS; GOLDING, Louise; SIENG, Bora; LUNDVALL, Steffi; B?EN, Claudia Alejandra; HNIDA, Kathrin; (68 pag.)WO2018/211276; (2018); A1;,
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