Tag: 6913-92-4

6913-92-4,6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the acetylene (1.1 eq) in 1,2-dichloroethane, was added CO2(CO)8 (1.1 eq) and the mixture was stirred 2 hours at room temperature. A solution of the pyrroline (1 eq) in 1,2-dichloroethane and the additive (dimethylsulfoxide or cyclohexylamine) (3.5 eq) were added and the mixture was heated at 83C for 20 hours. The reaction mixture was filtered through celite and washed with CH2Cl2. The filtrate was concentrated and the crude was purified by flash chromatography. From phenylacetylene (5.0 g, 48.3 mmol), Co2(CO)8 (16.5 g, 48.3 mmol), 1-benzyl-3-pyrroline (7.0 g, 43.9 mmol), dimethylsulfoxide (12.0 g, 153.8 mmol) and 1,2-dichloroethane (200 ml). Purification: silica gel, gradient dichloromethane to dichloromethane:methanol 1%, afforded the product (5.9 g, 46%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.72 (m, 2H), 7.65 (d, J=3Hz, 1H), 7.40-7.18 (m, 8H), 3.49-3.63 (AB system, 2H), 3.36 (m, 1H), 3.19 (d, J=9Hz, 1H), 2.94 (m, 1H), 2.83 (d, J=9Hz, 1H), 2.43 (t, J=9Hz, 1 H), 2.37 (t, J=9Hz, 1 H). 13C NMR (75 MHz, CDCl3) delta (ppm) 208.94, 159.74, 143.79, 138.30, 131.47, 128.45, 128.38, 128.34, 128.18, 58.91, 56.79, 55.89, 50.24, 42.58. MS (El+) m/z: 289.14 (M+).

The synthetic route of 6913-92-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1849772; (2007); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

6913-92-4, A mixture of 0.675 g (3.14 mMol) 7-bromo-5-fluorobenzofuran, 5.0 g (31.40 mMol)1-benzyl-3-pyrroline, 2.19 mL (12.56 mMol), N,N-diisopropylethylamine, 0.399 g (9.42 mMol) LiCl, 0.154 g (0.66 mMol) tri-2-furylphosphine, and 0.070 g (0.314 mMol) palladium diacetate in 10 mL N,N-dimethylformamide was heated under nitrogen at 100C for 48 hours. The mixture was diluted with 10 mL diethyl ether and filtered through celite. The filtrate was concentrated under reduced pressure and the oily residue was submitted to kugelrohr distillation to remove most of the pyrrole and pyrrolidine side-products. Flash chromatography of the residue (Et3N/Et2O/hexane 1:39:60) yielded 1-benzyl-3-(5-fluorobenzofur-7-yl)pyrrolidine (173 mg, 19%) as a colorless oil. HRMS calculated for C19H19FNO: 296.1450; found: 296.1437

The synthetic route of 6913-92-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; EP1204659; (2003); B1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

6913-92-4, To an ice-cooled solution of 1-benzyl pyrroline (0. 01 mol), 98% H2SO4 (0.012 mol), water (1.5 g), and acetone (10 mL) in a round bottom flask was added 77% m- CPBA (0. 013 mol) with stirring, and allowed to react for about 50 h at room temperature. After completion of the reaction (TLC monitor), acetone was evaporated under reduced pressure, and the mixture was neutralized by 1M NAOH, and extracted with toluene (30 mL X3). The precipitates that appeared were filtered, and the filtrate was repeatedly washed with water (30 mL x2). After the solvent was evaporated under reduced pressure, pure product was obtained in 77% yield via column chromatography (silica gel, CH2CL2 : EtOAc: MeOH, 7.5 : 2.00 : 0.5).

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; NORTHWESTERN UNIVERSITY; WO2005/26111; (2005); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6913-92-4

A solution of nitrone 11 (300 mg, 2.29 mmol) and N-benzyl-3-pyrroline 2 (0.8 mL, 4.20 mmol) in toluene (3 mL) was stirred for 1 h at 80 C under micro-wave irradiation. TLC (1:3 EtOAc/petroleum ether) showed complete conversion of the nitrone into a major product, and unidentified polar byproducts. The solvent was evaporated and the residue was subjected to silica gel column chromatography (mobile phase: 1:4 EtOAc/toluene) to afford cycloadduct (+-)-14 (390 mg, 58%). Colourless oil. Rf = 0.4 (1:4 EtOAc/toluene). 1H NMR (500 MHz, CDCl3) delta 7.35-7.20 (m, 5H, H-Ar), 4.60 (dd, 1H, J = 4.9 Hz, J = 7.4 Hz, H-4), 4.20 (q, 2H, J = 7.1 Hz, H-8), 3.70 (d, 1H, J = 13.2 Hz, NCH2Ph), 3.58 (d, 1H, J = 13.2 Hz, NCH2Ph), 3.25 (q, 1H, J = 7.1 Hz, H-3), 3.17 (br s, 1H, H-6), 3.00 (d, 1H, J = 11 Hz, H-5′), 2.94 (d, 1H, J = 9.8 Hz, H-2′), 2.78 (s, 3H, NCH3), 2.28 (br t, 1H, J = 7.6 Hz, H-2), 2.19 (br d, 1H, J = 6.6 Hz, H-5), 1.27 (t, 3H, J = 7.1 Hz, H-9). 1D NOE experiments with selective irradiations (H-3, H-4, or H-6), showed signals enhancements as follows: H-3 irradiation: enhancements of H-2: 4%, H-2′: 1.8%, H-4: 4%; irradiation of H-4: enhancements of H-3: 3.5%, H-5: 3.7%, H-5′: 1.9%; irradiation of H-6: enhancements of H-2: 1.3%, H-2′: 2.7%. 13C NMR (126 MHz, CDCl3) delta 170.03 (CO), 138.58 (C-ar), 128.73, 128.41, 127.17 (5CH-ar), 81.03 (C-4), 75.48 (C-6), 61.26 (C-8), 59.08 (C-11), 58.77 (C-5), 56.79 (C-2), 52.54 (C-3), 43.85 (NCH3), 14.24 (C-9). HRMS-ESI, positive mode: m/z calcd for C16H23N2O3 [M+H]+: 291.1703; found: 291.1702.

As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.

Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

6913-92-4, Cycloaddition of cyanonitrone 10 on 2 in order to obtain the heterobicycle 11: Cyanonitrone 10 (550 mg, 3.44 mmol) and benzyl-3-pyrroline 2 (13 ml, 6.83 mmol) are dissolved in toluene (4 ml) and stirred for 2 h at 80 C. under microwave irradiation (display temperature: 80 C.). The solvent is then evaporated before purification and separation on a silica column (eluent: AcOEt/toluene 1/10) of a regioisomer (60 mg, 6%) in order to obtain the expected racemic cycloadduct 11 (500 mg, 45%). Aspect: yellow oil. Rf=0.4 (EtOAc/toluene 1/4). 1H NMR (400 MHz, 60 C., toluene-D8): delta 7.3-7.0 (m, 10H), 4.28 (ddd, 1H, J=3.4 Hz, J=6.0 Hz, J=7.5 Hz, H-4), 4.17 (d, 1H, J=13.4 Hz, H-9), 3.81 (d, 1H, J=13.4 Hz, H-9?), 3.30 (d, 1H, J=13.1 Hz, H-8), 3.23 (d, 1H, J=13.1 Hz, H-8?), 3.06 (d, 1H, J=3.6 Hz, H-6), 2.79 (ddd, 1H, J=3.8 Hz, J=7.9 Hz, J=11.6 Hz, H-3), 2.47 (ddd, 1H, J=3.0 Hz, J=10.0 Hz, H-5), 2.24 (br m, 1H, H-5?), 2.16 (br m, 1H, H-2), 2.07 (br m, 1H, H-2?) ppm. 13C NMR (100 MHz, 60 C., toluene-D8): delta 139.3, 136.7, 129.7, 129.7, 129.0, 129.0, 128.8, 128.8, 128.8, 128.8, 128.1, 127.6, 116.5 (C-7), 81.4 C-4), 59.5 (C-8), 59.3 (3C, C-5, C-6, C-9), 57.0 (C-2), 53.0 (C-3) ppm. HRMS: m/z calcul. for C20H22N3O [M+H]+: 320.1757. found: 320.1767.

As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.

Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

Preparation of the Compound I.1: (alphaS,3R,4S) 4-hydroxy alpha-amino acetic 3-pyrrolidine acid or (alphaS,3R,4S) alpha-amino-(4-hydroxy-pyrrolidin-3-yl)acetic acid Cycloaddition of the nitrone 1 (corresponding to the compounds of formula (III)) on commercial N-Bn-3-pyrroline 2 (corresponding to the compounds of formula (IV)): synthesis of 3 (corresponding to the compounds of formula (II)): The nitrone 1 (392 mg, 1.64 mmol) [24, 25] and commercial N-Bn-3-pyrroline 2 in excess (314 mg, 1.97 mmol, 1.2 equiv.) are introduced into a flask adapted to a Biotage Initiator microwave reactor. After having filled the flask with argon, 2.5 ml of anhydrous toluene are poured therein. The flask, sealed with a septum and mounted in the microwave apparatus is irradiated with the instruction of maintaining a temperature of 140 C. for 2 h in order to totally convert the nitrone 1. Once the flask is cooled, the reaction crude product is concentrated and then purified by flash chromatography on a silica column (ethyl acetate) in order to lead to the cycloadduct 3 (625 mg, 1.57 mmol) with a yield of 96% and total stereoselectivity (the reaction was conducted on a scale of 5 grams with similar results). Single crystals of the compound 3 were obtained from a diethyl ether solution saturated with 3, left in the cold (freezer). Rf=0.48 (EtOAc). [alpha]D=+40.4 (c 1.1, CH2Cl2). 1H NMR (400 MHz, CDCl3): delta 7.37-7.20 (m, 5H, CH-ar), 4.59 (td, J=7.0 Hz, J=3.0 Hz, 1H, H-4), 3.71-3.49 (m, 3H, NCH2Ph, H-6), 3.42 (dd, J=10.3 Hz, J=6.6 Hz, 1H, H-3), 2.78 (dd, J=10.3 Hz, J=3.0 Hz, 1H, H-5), 2.75-2.69 (m, 4H, NCH3, H-2), 2.65 (dd, J=9.4 Hz, J=3.7 Hz, 1H, H-2′, 2.58 (dd, J=9.9 Hz, J=6.6 Hz, 1H, H-5′, 2.14-2.08 (m, 1H, H-9), 2.00 (dtt, J=12.9 Hz, J=6.5 Hz, J=3.3 Hz, 1H, H-10), 1.90-1.78 (m, 2H, H-11, H-12), 1.68-1.59 (m, 1H, H-12′), 1.48 (dt, J=13.5 Hz, J=6.7 Hz, 1H, H-15), 1.38 (dd, J=12.1 Hz, J=3.2 Hz, 1H, H-13), 1.18 (t, J=12.3 Hz, 1H, H-9′), 0.95-0.85 (m, 10H, H-11′, H-14, H-16) ppm. 13C NMR (100 MHz, CDCl3): delta 172.8 (C=O), 138.9 (CIV-ar), 128.6 (CH-ar), 128.3 (CH-ar), 127.1 (CH-ar), 88.0 (C-8), 79.6 (C-4), 71.9 (C-6), 59.6 (NCH2Ph), 59.4 (C-5), 59.3 (C-2), 49.1 (C-3), 48.2 (C-13), 41.0 (C-9), 35.0 (C-11), 29.0 (C-10), 25.9 (NCH3), 24.5 (C-15), 24.2 (CH3), 22.6 (C-12), 22.4 (CH3), 18.7 (CH3) ppm. HR-ESI-QToF MS (positive method): m/z calcul. for C24H36N3O2 [M+H]+ 398.2802. found 398.2806.

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

Example 16 2-benryl-5-tert butyl-1,2,3,3a-tetrahydrocyclopenta[c]pyrrol-4(6aH)-one. To a solution of 3,3-dimethyl-1-butyne (29 mg, 0.34 mmol) in 1,2-dichloroethane (1ml) cooled at 0C was added CO2(CO)8 (118 mg, 0.34 mmol) and the mixture was stirred 15 min at 0C and 40 minutes at room temperature. A solution of 1-benzyl-3-pyrroline (50 mg, 0.31 mmol) in 1,2-dichloroethane (1 ml) and dimethylsulfoxide (72 mul, 1.01 mmol) were added and the mixture was heated at 83C for 20 hours. The reaction mixture was filtered through celite and washed with CH2Cl2. The filtrate was concentrated and the crude was purified by flash chromatography: silica gel, dichloromethane, to afforded the product (11 mg, 13%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.29-7.17 (m, 5H), 7.08 (d, J=3Hz, 1H), 3.59-3.47 (AB system, 2H), 3.17 (m, 1H), 3.04 (d, J=9Hz, 1H), 2.72 (m, 1H), 2.68 (d, J=9Hz, 1H), 2.35 (t, J=9Hz, 1H), 2.30 (t, J=9Hz, 1H), 1.20 (s, 9H). 13C NMR (75 MHz, CDCl3) delta (ppm) 209.28, 156.44, 154.52, 128.27, 128.19, 126.88, 58.69, 58.78, 56.15, 50.23, 42.00, 31.72, 28.33,. MS (El+) m/z: 269.17 (M+).

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1849772; (2007); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3,3-dimethyl-1-butyne (29 mg, 0.34 mmol) in 1,2-dichloroethane (1ml) cooled at 0C was added Co2(CO)8 (118 mg, 0.34 mmol) and the mixture was stirred 15 min at 0C and 40 minutes at room temperature. A solution of 1-benzyl-3-pyrroline (50 mg, 0.31 mmol) in 1,2-dichloroethane (1 ml) and dimethylsulfoxide (72 mul, 1.01 mmol) were added and the mixture was heated at 83C for 20 hours. The reaction mixture was filtered through celite and washed with CH2Cl2. The filtrate was concentrated and the crude was purified by flash chromatography: silica gel, dichloromethane, to afforded the product (11 mg, 13%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.29-7.17 (m, 5H), 7.08 (d, J=3Hz, 1H), 3.59-3.47 (AB system, 2H), 3.17 (m, 1H), 3.04 (d, J=9Hz, 1H), 2.72 (m, 1H), 2.68 (d, J=9Hz, 1H), 2.35 (t, J=9Hz, 1H), 2.30 (t, J=9Hz, 1H), 1.20 (s, 9H). 13C NMR (75 MHz, CDCl3) delta (ppm) 209.28, 156.44, 154.52, 128.27, 128.19, 126.88, 58.69, 58.78, 56.15, 50.23, 42.00, 31.72, 28.33, MS (EI+) m/z: 269.17 (M+).

As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1849770; (2007); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

(a) 40.0 g (0.25 mol) of N-benzyl-3-pyrroline are dissolved in 400 ml of benzene. 53.0 g (0.25 mol) of 2,2,2-trichloroethyl chloroformate are introduced into this solution in the course of 30 minutes, at 0 and under a nitrogen atmosphere. The reaction mixture is stirred for a further 1 hour at 0, then washed at room temperature twice with, in each case, 100 ml of a mixture of water and 2 N hydrochloric acid (3:1) and then twice with water, dried over sodium sulphate and evaporated under a water pump vacuum. The oily residue is distilled under a high vacuum and, after 24 g of benzyl chloride has been separated off, N-(beta,beta,beta-trichloroethoxycarbonyl)-3-pyrroline with a boiling point of 84-85 C./0.12 mm Hg is obtained.

As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.

Reference£º
Patent; Ciba-Geigy Corporation; US4160837; (1979); A;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Nitrone 12 (149 mg, 0.72 mmol) and N-benzyl-3-pyrroline 2 (170 muL, 0.89 mmol) were dissolved in toluene (2 mL) containing a few drops of CH2Cl2 for solubilization. Cycloaddition was completed after stirring for 1 h at 80 C under micro-wave irradiation. The solvent was evaporated under reduced pressure and purification of the residue by silica gel column chromatography (mobile phase: 1/9 EtOAc/toluene) afforded cycloadduct (+-)-16 (180 mg, 68% yield). Colourless oil; Rf = 0.6 (EtOAc/toluene 1/4). 1H NMR (500 MHz, 50 C, CDCl3) delta 7.25-7.45 (m, 10H, H-Ar), 4.62 (dd, 1H, J = 4.9 Hz, J = 7.6 Hz, H-4), 4.22 (d, 1H, 2J = 13.7 Hz, ONCH2Ph), 4.12 (dq, 2H, 3J8,9 = 7.1 Hz, J = 1.6 Hz, H-8), 4.05 (d, 1H, 2J = 13.7 Hz, ONCH2Ph), 3.68 (d, 1H, 2J = 13.2 Hz, NCH2Ph), 3.61 (d, 1H, 2J = 13.2 Hz, NCH2Ph), 3.39 (d, 1H, 3J = 7.0 Hz, H-6), 3.28 (q, 1H, 3J = 7.0 Hz, H-3), 3.00 (d, 1H, 3J = 11 Hz, H-5′), 2.95 (d, 1H, 3J = 9.6 Hz, H-2′), 2.32 (br s, 1H, H-2), 2.21 (br s, 1H, H-5), 1.24 (t, 3H, 3J = 7.1 Hz, H-9). 13C NMR (126 MHz, 50 C, CDCl3) delta 170.28 (C=O), 138.64, 136.93, 129.50, 128.76, 128.44, 128.30, 127.47, 127.23 (12C-ar), 81.05 (C-4), 73.09 (C-6), 61.24 (C-8), 60.92 (C-10), 59.06 (C-11), 58.88 (C-5), 56.94 (C-2), 52.23 (C-3), 14.23 (C-9). 2D NOE correlations were confirmed by 1D NOE experiments with selective irradiations (H-3, H-4, or H-6), showing signals enhancements as follows: H-3 irradiation: enhancements of H-2: 3.7%, H-2′: 1.7%, H-4: 5.2%; irradiation of H-4: enhancements of H-3: 3.9%, H-5: 2.9%, H-5′: 2.0%, H-6: 1.0%; irradiation of H-6: enhancements of H-2: 0.9%, H-2′: 3.9%, H-4: 1.4%. HRMS-ESI, positive mode: m/z calcd for C22H27N2O3 [M+H]+: 367.2016; found: 367.2009.

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem