Electric Literature of 2435-36-1,Some common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, molecular formula is C9H14O4, 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.
Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate. n-Butyllithium (2.5 M in hexane, 419.0 mL, 1048 mmol) was added slowly to a solution of diisopropylamine (152 mL, 1090 mmol) and anhydrous THF (1000 mL) at -78 C. (dry ice/acetone) under N2. Next, the reaction was stirred for 0.5 hours at 0 C. before cooling to -78 C. DMPU (404 mL, 3350 mmol) was added via an addition funnel. Then a solution of dimethyl cyclopentane-1,3-dicarboxylate (78.0 g, 419 mmol) and anhydrous THF (300 mL) was added slowly via an addition funnel. The reaction was warmed to 0 C. and stirred for 30 minutes, then cooled to -78 C. and treated with a solution of 1-bromo-2-chloroethane (59.0 mL, 712 mmol) and anhydrous THF (200 mL). The reaction was allowed to warm slowly to room-temperature and was stirred for 12 hours at room-temperature. The reaction was quenched with saturated aqueous ammonium chloride (400 mL). The reaction was diluted with ethyl acetate (500 mL), the organic layer separated, and the aqueous layer was further extracted with ethyl acetate (2¡Á500 mL). The combined organic extracts were washed with brine (2¡Á300 mL), dried over anhydrous MgSO4, filtered, and concentrated to dryness. The residue was filtered through a pad of silica gel and washed with ethyl acetate (2000 mL). The filtrate was concentrated to dryness and the residue was purified by flash column chromatography (petroleum ether/ethyl acetate, 30:1 to 20:1, gradient elution) to provide the title compound (48.5 g, 54%) as white solid. 1H NMR (400 MHz, CDCl3): delta 3.69 (s, 6H), 2.08-1.99 (m, 4H), 1.91 (s, 2H), 1.73-1.63 (m, 4H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl cyclopentane-1,3-dicarboxylate, its application will become more common.
Reference:
Patent; Janssen Pharmaceutica NV; Koudriakova, Tatiana; Kreutter, Kevin D.; Leonard, Kristi; Rizzolio, Michele C.; Smith, Russell C.; Tichenor, Mark S.; Wang, Aihua; (40 pag.)US2018/170931; (2018); A1;,
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