Electric Literature of 2435-36-1, The chemical industry reduces the impact on the environment during synthesis 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, I believe this compound will play a more active role in future production and life.
Step B: 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) underN2. Next, the reaction was stirred for 0.5 hours at 0 C before cooling to -78 C. DIVIPU (404 mL, 3350mmol) 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 -78C 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 x 500 mL). The combined organic extracts were washed with brine (2 x 300 mL), dried overanhydrous 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. ?H NIVIR (400MHz, CDC13): 3.69 (s, 6H), 2.08 – 1.99 (m, 4H), 1.91 (s, 2H), 1.73 – 1.63 (m, 4H)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Dimethyl cyclopentane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis M.; CHAI, Wenying; KOUDRIAKOVA, Tatiana; KRAWCZUK, Paul J.; KREUTTER, Kevin D.; LEONARD, Kristi; RIZZOLIO, Michele C.; SEIERSTAD, Mark; SMITH, Russel C.; TICHENOR, Mark S.; VENABLE, Jennifer D.; WANG, Aihua; (452 pag.)WO2018/112382; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics