Category: 1128-00-3

Synthetic Route of 1128-00-3, A common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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.

To a solution of ethyl 2-aminocyclohex-1-enecarboxylate (33) (3.33 g, 19.7 mmol) and pyridine (2.33 g, 29.5 mmol) in dry THF (50 ml) at -5 C slowly within 1 h 2-bromoacetyl bromide (3.93 g, 19.5 mmol) was added. The reaction mixture was stirred at the same temperature for 45 min. and partitioned between ethyl acetate (50 ml) and satd NaHCO3 (50 ml). The water phase was extracted with ethyl acetate (3 × 30 ml). The organic extracts were combined, and successively washed with satd NaHCO3 solution (50 ml), water (2 × 50 ml), satd NaCl solution (50 ml), and dried (Na2SO4). The solvent was evaporated, the residue was mixed with ethyl acetate (50 ml), and the solid material was filtered off. The filtrate was evaporated to dryness and the residue was dried in vacuo over P2O5 to give 5.00 g (88%) of compound 34 as a brown oil, which was immediately utilized in the next step. 1H NMR (CDCl3) delta: 1.30 (t, J = 7.1 Hz, 3H), 1.55-1.68 (m, 4H), 2.30-2.36 (m, 2H), 2.90-2.96 (m, 2H), 3.86 (s, 2H), 4.21 (q, J = 7.1 Hz, 2H), 12.08 (br s, 1H). GCMS m/z: 289.0 M+.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
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Synthetic Route of 1128-00-3, These common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, 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.

In a 2000 ml flask were charged ethyl 2-aminocyclohexene-1-carboxylate (80.0 g, 472.8 mmol), pyridine (37.4 g, 472.8 mmol), and acetonitrile (190 ml), and the mixture was dissolved by heating to 40 C. While keeping the mixture at 40-50 C., a solution (126 ml) of benzyl chloride (63.14 g, 449.2 mmol) in acetonitrile was added dropwise. The mixture was stirred at 50-60 C. for 1.5 hr, cooled, and water (631 ml) was added dropwise at 20-30 C. over 30 min. After stirring at the same temperature for 30 min, the precipitate was collected by filtration and washed with water (631 ml). The obtained powder was dried under reduced pressure at 60 C. yield 119.62 g, 97%. [0533] Anal. calcd. for C16H19NO3, C, 70.31; H, 7.01; N, 5.12. found C, 70.29; H, 7.15; N, 5.08. HR-Ms calcd. for C16H19NO3, 274.1438 ([M+H]+). found, 274.1428 ([M+H]+).

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1128-00-3,Some common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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.

General procedure: To a solution of appropriate carboxylic acid 44a-d (1.0 mmol) in dichloromethane (6 ml) oxalylchloride (3.0 mmol) and a drop of DMF were added. The reaction mixture was stirred at ambient temperature for 40 min and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (6 ml), and under argon to the obtained solution was added a mixture of ethyl 2-aminocyclohex-1-enecarboxylate (33) (1.1 mmol) and triethylamine (1.1 mmol) in dichloromethane (3 ml). The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane, washed successively with NaHCO3 solution, brine, and dried (Na2SO4). The solvent was removed and the residue was purified as indicated below to give crystalline compounds 45a-d.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1128-00-3, Recommanded Product: Ethyl 2-aminocyclohex-1-enecarboxylate

To the intermediate alpha-methylacid bromothiazole above (197 mg, Compound 52 in Scheme 11) in dichloromethane (10 mL) was added one drop of DMF, and then a solution of oxalyl chloride (1.6 mL, 2 N in dichloromethane). The mixture was warmed to room temperature and stirred for 1 h. The resulting mixture was concentrated in vacuo and then dissolved in dichloromethane (10 mL). To the resulting solution was then added the common 2-aminocyclohex-1-ene-1-carboxylate ester (400 mg). The resulting mixture was stirred overnight. The crude material was purified by Biotage (5-10% ethyl acetate in hexane) to give the amide as a colorless oil.

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, Ethyl 2-aminocyclohex-1-enecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Raghavan, Subharekha; Colletti, Steven L.; Ding, Fa-Xiang; Shen, Hong; Tata, James R.; Lins, Ashley Rouse; Smenton, Abigail Lee; Chen, Weichun; Schmidt, Darby Rye; Tria, George Scott; US2006/293364; (2006); A1;,
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Reference of 1128-00-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-Pentynoic acid (15) (1.00 g, 10.19 mmol) in DCM (20 ml) under argon atmosphere at rt was treated with DMF (39 ll,0.51 mmol) and oxalyl chloride (2.22 ml, 25.48 mmol). The mixture was stirred for 40 min and the volatiles were evaporated. The residue was dissolved in DCM (3 ml) and the obtained solution was added to a mixture of ethyl 2-aminocyclohex-1-ene-1-carboxylate(0.10 g, 0.59 mmol) and DIPEA (1.76 ml, 10.2 mmol) in DCM (15 ml) at 5 C to 2 C under argon atmosphere. The mixture was stirred for 1 h at 0 C and warmed to rt. The mixture was diluted with DCM, washed with saturated NH4Cl, brine, and dried over Na2SO4. The solvent was evaporated and the residue was chromatographed on silica gel (EtOAc in petroleum ether, 1:20 to1:10) to afford a white solid. Recrystallization from n-heptane gave the product 18 (1.20 g). The filtrate after crystallization was concentrated and the residue was chromatographed on Biotage (EtOAcin petroleum ether, 2-20%) to give the product (0.25 g); the combined yield was 1.45 g, 57%. 1H NMR (300 MHz, CDCl3) d: 11.66(s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.03-2.92 (m, 2H), 2.65-2.49 (m,4H), 2.36-2.25 (m, 2H), 1.97 (t, J = 2.3 Hz, 1H), 1.70-1.54 (m, 4H),1.30 (t, J = 7.1 Hz, 3H). 13C NMR (75 MHz, CDCl3) d: 170.1, 169.6,152.1, 104.9, 82.8, 69.2, 60.4, 37.2, 28.7, 24.3, 22.0, 21.8, 14.6,14.4. LCMS (ESI) m/z 250.18 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-aminocyclohex-1-enecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4314 – 4329;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: 5-phenylpent-2-enoic acid (13) (0.18 g, 1.02 mmol) in DCM(2 ml) under argon atmosphere at rt was treated with a catalytic amount of DMF (1 drop) and oxalyl chloride (0.26 ml, 3.06 mmol). The mixture was stirred for 40 min and the volatiles were evaporated. The residue was dissolved in DCM (2 ml) and to the obtained solution at 0 C a mixture of ethyl 2-aminocyclohex-1-ene-1-carboxylate(0.26 g, 1.54 mmol) and triethylamine (0.14 ml,1.00 mmol) in DCM (1 ml) was added dropwise over 5 min. The mixture was stirred for 40 min at rt, then the mixture was supplemented with DCM, washed with saturated NH4Cl solution, brine,dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel (EtOAc in petroleum ether, 1:10 to1:6) to give crude ethyl (E)-2-(5-phenylpent-2-enamido)cyclohex-1-ene-1-carboxylate (0.21 g) as a colorless oil. 1H NMR(300 MHz, CDCl3) d: 11.71 (s, 1H), 7.33-7.16 (m, 5H), 6.92 (dt,J = 15.3, 6.8 Hz, 1H), 5.92 (dt, J = 15.3, 1.5 Hz, 1H), 4.19 (q,J = 7.1 Hz, 1H), 3.09-2.98 (m, 2H), 2.85-2.69 (m, 2H), 2.59-2.45(m, 2H), 2.39-2.25 (m, 2H), 1.73-1.56 (m, 4H), 1.30 (t, J = 7.1 Hz,3H). LCMS (ESI) m/z: 328.37 [M+H]+. The oil was dissolved in a mixture of THF (2 ml) and EtOH (1 ml) and to the obtained solution 2 N NaOH (0.92 ml, 1.84 mmol) was added. The mixture was stirred for 16 h at rt followed by stirring for 5 h at 50 C. The reaction mixture was cooled to rt and acidified to pH 4 with 1 N HCl. The solvents were evaporated and the residue was partitioned between DCM and water. The organic layer was dried over Na2SO4, evaporated, and the residue was chromatographed on silica gel (MeOH in DCM, 1:20) to give an oily solid. The solid was triturated with EtOAc petroleum ether mixture (1:4), filtered, and dried in vacuo to give the product 3 (44 mg, 14%, calculated with respect to 13) as white crystals.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4314 – 4329;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 1128-00-3, A common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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.

To a solution of ethyl 2-aminocyclohex-1-enecarboxylate (33) (3.33 g, 19.7 mmol) and pyridine (2.33 g, 29.5 mmol) in dry THF (50 ml) at -5 C slowly within 1 h 2-bromoacetyl bromide (3.93 g, 19.5 mmol) was added. The reaction mixture was stirred at the same temperature for 45 min. and partitioned between ethyl acetate (50 ml) and satd NaHCO3 (50 ml). The water phase was extracted with ethyl acetate (3 ¡Á 30 ml). The organic extracts were combined, and successively washed with satd NaHCO3 solution (50 ml), water (2 ¡Á 50 ml), satd NaCl solution (50 ml), and dried (Na2SO4). The solvent was evaporated, the residue was mixed with ethyl acetate (50 ml), and the solid material was filtered off. The filtrate was evaporated to dryness and the residue was dried in vacuo over P2O5 to give 5.00 g (88%) of compound 34 as a brown oil, which was immediately utilized in the next step. 1H NMR (CDCl3) delta: 1.30 (t, J = 7.1 Hz, 3H), 1.55-1.68 (m, 4H), 2.30-2.36 (m, 2H), 2.90-2.96 (m, 2H), 3.86 (s, 2H), 4.21 (q, J = 7.1 Hz, 2H), 12.08 (br s, 1H). GCMS m/z: 289.0 M+.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1128-00-3,Some common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 170 mg of ethyl 2-aminocyclohex-1-enecarboxylate as synthesized in Step 7-1-B in 5 ml of pyridine, 70 mg of phosphorus trichloride was added under cooling with ice, followed by 15 minutes’ stirring. Raising the temperature to room temperature, 327 mg of 5-(4-quinoline-2-ylpiperazin-1-yl)hexanoic acid as synthesized in above Step 7-14-C was added to the solution and stirred for 3 hours. Distilling the pyridine off under reduced pressure, the residue was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 182 mg (38%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylate. 1H-NMR(CDCl3)delta:11.61(br s,1H),7.86(d,J=8.9Hz,1H), 7.68(d,J=8.5Hz,1H),7.57(d,J=7.7Hz,1H), 7.51(ddd,J=1.2Hz,6.9Hz,8.1Hz,1H),7.22~7.18(m,1H), 6.96(d,J=9.3Hz,1H),4.14(q,J=6.9Hz,2H),3.80~3.70(m,4H), 2.98~2.95(m,2H),2.75~2.65(m,3H),2.64~2.56(m,2H), 2.34(t,J=7.3Hz,2H),2.31~2.28(m,2H),1.81~1.70(m,2H), 1.69~1.56(m,6H),1.26(t,J=6.9Hz,3H),1.01(d,J=6.6Hz,3H) Mass,m/e:478(M+),157(base)

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP1724267; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics