Category: 2435-36-1

Synthetic Route of 2435-36-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution a solution of LDA (33.6 mL, 67.1 mmol) in 10 mL THF was added a solution of dimethyl cyclopentane-1, 3-dicarboxylate (5 g, 26.9 mmol) in 10 mL THF under N2 protection dropwise at -78 and stirred at -78 for 25 mimutes. To the solution was added iodomethane (9.53 g, 67.1 mmol) dropwise and stirred at ROOM TEMPERATURE for another 16 houtrs. The solution was poured into water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated in vacuo to give the title compound. 1H NMR (400MHz, CDCl3) : delta3.66 (major) , 3.63 (minor) (s, 6H) , 2.29-2.20 (m, 2H) , 2.12 (s, 2H) , 1.65-1.55 (m, 2H) , 1.30 -1.20 (m, 6H) ppm.

The synthetic route of Dimethyl cyclopentane-1,3-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ANDRESEN, Brain M.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (111 pag.)WO2016/106624; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2435-36-1 as follows. Recommanded Product: Dimethyl cyclopentane-1,3-dicarboxylate

Diisopropylamine (210.0g, 201.0mmol), tetrahydrofuran (5.0L) was added to a 10L four-necked flask with mechanical stirring and thermometer. 80.0ml / 2.5M, 200.0mmol), keep -10 -60 and stir for 15min, add hexamethylphosphonic acid triamine (370.0g, 207.0mmol), control temperature -10 -60 , add cyclopentane dropwise -1,3-Dicarboxylic acid methyl ester (150.0g, 80.6mmol), after incubation and stirring for half an hour, dropwise add diiodomethane (210.0g, 80.6mmol), return to room temperature for 20min, dropwise add acetic acid (50ml) to quench After the reaction, 2.0L of 2N hydrochloric acid was added, the liquid was stirred and separated, and the organic phase was collected and concentrated to obtain the crude product, which was distilled under reduced pressure with an oil pump. Fractions around 100 C to 105 C were collected to obtain 95.0g of dicyclohexane [2.1.1] hexane- Dimethyl 1,4-dicarboxylate is a light yellow liquid with a purity of 98% and a yield of 59%.

According to the analysis of related databases, 2435-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Zhou Miao; Yu Jurong; (5 pag.)CN110878019; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products 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.

To a solution of HMPA (13.08 mL, 75 mmol) and LDA (13.43 mL, 26.9 mmol) in THF (30 mL) was added a solution of dimethyl cyclopentane-1, 3-dicarboxylate (2 g, 10.74 mmol) in 10 mL THF dropwise over 30 minutes at -78 under N2protection and stirred at one point for another 30 minutes. The solution was warmed to 0 and stirred at one point for 1 hour. The solution was cooled to -78 and added a solution of 1-bromo-2-chloroethane (1.848 g, 12.89 mmol) in 10 mL THF dropwise. The solution was stirred at -78 for 1 hour and warmed to RT. Afrer stirred for 16 hours, the solution was added 1N HCl and extracted with EtOAc. The combined organic layer was dried over Na2SO4, concentrated in vacuo to give the title compound.1H NMR (CDCl3400 MHz) : 3.67 (s, 6H) , 2.01 (d, J6.7 Hz, 4H) , 1.89 (s, 2H) , 1.66 (d, J6.7 Hz, 3H)

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2435-36-1, These common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, its 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.

Preparation of Bicyclic Amine Intermediate 3 (BAI-3) dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylateFreshly prepared lithium diisopropylamide (15 mL of n-butyllithium (2.5 M solution in hexane) and 5 mL of diisopropylamine were mixed at -30 C. in 50 mL of tetrahydrofuran) was cooled to -78 C. under nitrogen and stirred for 30 minutes. To a solution of dimethyl cyclopentane-1,3-dicarboxylate (2.67 g, 14.37 mmol) in tetrahydrofuran (12 mL) was drop added above freshly lithium diisopropylamide solution over 10 minutes (-75 C.-70 C.). The cold bath was then removed and the mixture was allowed to warm to 0 C. and maintained at that temperature for 20 minutes before being cooled to -80 C. A solution of 1-bromo-2-chloroethane (2 mL, 24 mmol) in tetrahydrofuran (25 mL) was added slowly to the reaction mixture over 35 minutes (-75 C.-70 C.). The reaction solution was then allowed to stir overnight with gradual warming to room temperature. The reaction was quenched by addition of saturated NH4Cl solution (20 mL). After removal of the solvent, 200 mL of ethyl acetate was added. The organic phase was washed with 2 N HCl (120 mL¡Á2), washed with brine and then dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/petroleum ether=1/10) to afford the titled compound. 1H NMR (400 MHz, CDCl3), delta (ppm): 3.68 (s, 6H), 2.022.03 (m, 4H), 1.91 (s, 2H), 1.68 (s, 4H); LCMS (ESI+) m/z 213.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2435-36-1.

Reference:
Patent; ABBOTT LABORATORIES; US2010/267738; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics