Category: 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

Cyanonitrone 13 (550 mg, 3.44 mmol) and N-benzyl-3-pyrroline2 (1.3 mL, 6.83 mmol) were dissolved in toluene (4 mL) and themediumwas stirred for 2 h at 80 C under micro-waves irradiation.The solvent was removed under reduced pressure before purificationby silica gel column chromatography (eluent: EtOAc/toluene 1/10). This allowed the separation of a minor more mobileregioisomer (60 mg, 6%) from the main racemic cycloadduct expected(¡À)-17 (500 mg, 45%). Compound (¡À)-17: Yellowish oil.Rf 0.4 (1:4 EtOAc/toluene). 1H NMR (500 MHz, 80 C, toluene-d8)d 7.4e7.0 (m, 10H, HeAr), 4.28 (ddd, 1H, J 3.4 Hz, J 6.0 Hz,J 7.5 Hz, H-4), 4.15 (d, 1H, J 13.4 Hz, H-8), 3.80 (d, 1H, J 13.4 Hz,H-8), 3.29 (d, 1H, J 13.1 Hz, H-9), 3.23 (d, 1H, J 13.1 Hz, H-9), 3.07(d, 1H, J 3.6 Hz, H-6), 2.79 (ddd, 1H, J 4.0 Hz, J 7.8 Hz,J 11.6 Hz, H-3), 2.48 (dd, 1H, J 3.1 Hz, J 10.1 Hz, H-50), 2.22 (br s,1H, H-5), 2.17 (br m, 1H, H-20), 2.09 (br m, 1H, H-2). 1D NOE experimentswith selective irradiations (H-3, H-4, or H-6), showedsignals enhancements as follows: H-3 irradiation: enhancements ofH-2: 2.5%, H-2?: 1.9%, H-4: 2%, H-6: 1.1%; irradiation of H-4: enhancementsof H-3: 2.1%, H-5: 1.9%, H-5?: 1.4%; irradiation of H-6:enhancements of H-2: 2%, H-2?: 1.8%. 13C NMR (126 MHz, 80 C,toluene-d8): d 139.8 (Caear), 137.2 (Ca?-ar), 130.2, 129.5, 129.4,129.3, 128.6, 128.1 (10C-ar), 116.9 (C-7), 81.9 (C-4), 60.0 (C-9), 59.9(C-6), 59.8, 59.7 (C-5, C-8), 57.5 (C-2), 53.6 (C-3). HRMS-ESI, positivemode: m/z calcd for C20H22N3O [MH]: 320.1757; found:320.1767.Compound (¡À)-18: yellow clear oil. Rf 0.6 (1/4 EtOAc/toluene).1H NMR (500 MHz, toluene-d8) d 7.5e7.0 (m, 10H, HeAr), 4.40 (dd,1H, J 4.7 Hz, J 7.7 Hz, H-4), 3.71 (d, 1H, J 8.1 Hz, H-6), 3.39 (s,2H, H-9), 3.20 (d, 1H, J 17.2 Hz, H-7), 3.01 (d, 1H, J 10.8 Hz, H-50),2.77 (d, 1H, J 17.2 Hz, H-7), 2.71 (d, 1H, J 9.7 Hz, H-20), 2.64 (app.q, 1H, J 7.3 Hz, H-3), 1.73 (m, 2H, H-2, H-5). 13C NMR (126 MHz,toluene-d8) d 140.02 (Caear), 138.41 (Ca?-ar), 129.84,129.35, 129.35,129.31, 128.93, 128.02 (10C-ar), 115.00 (C-8), 82.19 (C-4), 76.02 (C-6), 59.54 (C-9), 59.28 (C-5), 58.04 (C-3), 56.60 (C-2), 42.16 (C-7). 2DNMR (HMBC) showed correlations between H-6 and aromaticcarbons, as well as correlations between methylene H-7 and C-8 inthe nitrile group. 1D NOE experiments with selective irradiations(H-3, H-4, or H-6), showed signals enhancements as follows: H-3irradiation: enhancements of H-2: 4.6%, H-4: 4.2%, H-6: 1.1%, HeAr:3.5%; irradiation of H-4: enhancements of H-3: 3.8%, H-5: 4.1%, H-5?: 1.2%; irradiation of H-6: enhancements of H-2?: 2.9%, H-5?: 0.3%,HeAr: 5.4%. HRMS-ESI, positive mode: m/z calcd for C20H22N3O[MH]: 320.1757; found: 320.1750.

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

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

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, Example 26 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1-benzyl-4-hydroxy-pyrrolidin-3-yl)-amide Preparation of 4-Amino-1-benzyl-pyrrolidin-3-ol Step 1: To an ice-cooled solution of 26a (4.77 g, 30 mmol), 98% H2SO4 (1.95 mL), H2O (4.5 mL) and acetone (30 mL) was added 85% mCPBA (7.91 g, 39 mmol) with stirring. The mixture was allowed to react for 48 hrs at r.t. Acetone was evaporated and the mixture was neutralized with 1N aq. NaOH and extracted with toluene. The organic phase was dried over anhy. MgSO4 and evaporated. The residue was purified by column chromatography (EA:PE=1:4) to provide 26b (2.0 g, 38%).

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

Reference£º
Patent; Xcovery, Inc.; US2009/76005; (2009); 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

6913-92-4, Was synthesised according to published methods:. To a solution of 1-benzyl-3-pyrroline (5.0 g, 31.40 mmol) in methanol (20 ml) cooled at 0C, water was added (5 ml) and H2S04 96% (2 ml). The solution was stirred 5 min. and 3-chloroperoxybenzoic acid (10.0 g, 40.56 mmol) was added in portions. The suspension was stirred at r.t. for 18 h. Methanol was evaporated and the aquose solution was neutralized with aq. NaOH 10 % until pH=7. The suspension was extracted with dichloromethane and the organic phase was washed with water and saturated solution of NaCl, dried over Na2SO4, filtered and concentrated to afford pure product (4.35 g, 80%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.49-7.23 (m, 5H), 3.81 (s, 2H), 3.66 (s, 2H), 3.23 (d, J=12Hz, 2H), 2.72 (d, J=12Hz, 2H).

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.; EP1849781; (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

(2) To a solution of triethylamine (4.18 mL) and formic acid (0.384 mL) in N,N-dimethylformamide (20mL) were added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (205 mg), Compound 3 (1.90 g), Compound 4 (3.98 g), and N,N-dimethylformamide (10 mL), and the mixture was stirred at 95C for 2 hours. To the reaction mixture were added ethyl acetate and water at room temperature, stirred, and then extracted with ethyl acetate. The resultant organic layer was washed with water, dried, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=100:0-50:50) to give racemic Compound 5 (1.14 g) as a pale yellow viscous material. MS (APCI): m/z 461 [M+H]+

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

Reference£º
Patent; Mitsubishi Tanabe Pharma Corporation; YAMAMOTO, Yasuo; SATO, Atsushi; MOROKUMA, Kenji; SHITAMA, Hiroaki; ADACHI, Takashi; MIYASHIRO, Masahiko; (260 pag.)EP3150578; (2017); 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

6913-92-4, Example 2Synthesis of 3-benzyl-6-oxa-3-aza-bicyclo[3.1.0]hexane (1-2) 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 ¡Á3). The precipitates that appeared were filtered, and the filtrate was repeatedly washed with water (30 mL ¡Á2). 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).

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

Reference£º
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (2008); 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, Cycloaddition of the nitrone 7 on benzyl-3-pyrroline 2 in order to obtain the heterobicycle 8: The nitrone 7 (300 mg, 2.29 mmol) and benzyl-3-pyrroline 2 (0.8 ml, 4.20 mmol) are dissolved in toluene (3 ml) and stirred for 1 h at 80 C. with microwave irradiation. TLC (AcOEt/petroleum ether 1/3) shows total transformation of the nitrone. The solvent is then evaporated before purification of the cycloadduct 8 (390 ring, 58%) on a silica column (eluent: AcOEt/toluene 1/4) which removes the more polar compounds also formed. Aspect: colorless oil. Rf=0.4 (EtOAc/toluene 1/4). 1H NMR (500 MHz, CDCl3): delta 7.35-7.2 (m, 5H, H-Ar), 4.60 (dd, 1H, 3J=4.9 Hz, J=7.4 Hz, H-4), 4.20 (q, 2H, 3J=7.1 Hz, H-8, H-8?), 3.7 (d, 1H, 2J=13.2 Hz, H-11), 3.58 (d, 1H, 2J=13.2 Hz, H-11?), 3.24 (q, 1H, 3J=7.1 Hz, H-3), 3.16 (br s, 1H, H-6), 3.00 (d, 1H, 3J=11 Hz, H-5), 2.94 (d, 1H, 3J=9.8 Hz, H-2), 2.78 (s, 3H, NCH3), 2.28 (br s, 1H, H-2?), 2.19 (br s, 1H, H-5?), 1.27 (t, 3H, 3J=7.1 Hz, H-9) ppm. 13C NMR (126 MHz, CDCl3): delta 170.03 (C-7), 138.58, 128.73, 128.41, 127.17 (C-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) ppm. HRMS ESI: m/z calcul. for C16H23N2O3 [M+H]+: 291.1703. found: 291.1702.

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

Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); 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

6913-92-4, a 5-benzyl-3-(tetrahydropyran-2-yloxymethyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole To a solution of 1-benzyl-2,5-dihydro-1H-pyrrole (13.5 g, 84.8 mmol) in benzene (150 mL) was added 2-(2-nitroethoxy)tetrahydropyran (37 g, 211.2 mmol) and triethylamine (5.4 mL, 38.4 mmol). The solution was heated to reflux and phenyl isocyanate (37.8 mL, 347.8 mmol) was slowly added over 2 hours. After the addition was complete, the mixture was refluxed overnight and the resulting precipitate removed by filtration. The filtrate was concentrated in vacuo and the residue purified by column chromatography eluding with ethyl acetate:hexanes (1:4), to obtain 19.5 g the title compound. 1H NMR (200 MHz, CDCl3) delta 7.38-7.18 (m, 5H), 5.10-4.98 (m, 1H), 4.68-4.58 (bs, 1H), 4.50-4.18 (m, 2H), 3.86-3.42 (m, 5H), 3.25-3.05 (m, 2H), 2.44-2.24 (rA, 2H), 1.82-1.38 (m, 6H).

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

Reference£º
Patent; Ellsworth, Edmund Lee; Kerschen, James Alan; Powell, Sharon Anne; Sanchez, Joseph Peter; Showalter, Howard Daniel Hollis; Stier, Michael Andrew; Tran, Tuan Phong; US2003/114666; (2003); 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

General procedure: In a Biotage Initiator 2-5 mL vial, nitrone 1 (392 mg, 1.64 mmol) and N-benzyl-3-pyrroline 2 (314 mg, 1.97 mmol, 1.2 eq) were introduced. The vial was flushed with argon and 2.5 mL of anhydrous toluene was added (c = 0.66 mM). The vial was sealed with a septum cap and was sonicated for 20 s. The resulting mixture was irradiated by microwaves (temperature: 140 C). TLC monitoring (EtOAc) showed full conversion after 2 h. After the crude mixture was concentrated, the crude product was purified by flash silica gel column chromatography (EtOAc) to afford cycloadduct 3 (625 mg, 1.57 mmol, 96%) with no traces of other isomer. Monocrystals ofcompounds 3 were obtained from a saturated Et2O solution cooledin a freezer. Rf 0.48 (EtOAc). [a]D 40.4 (c 1.1, CH2Cl2). 1H NMR(400 MHz, CDCl3) d 7.37e7.20 (m, 5H, CH-ar), 4.59 (td,1H, J 7.0 Hz,J 3.0 Hz, H-4), 3.71e3.49 (m, 3H, NCH2Ph, H-6), 3.42 (dd, 1H,J 10.3 Hz, J 6.6 Hz, H-3), 2.78 (dd, 1H, J 10.3 Hz, J 3.0 Hz, H-5), 2.75e2.69 (m, 4H, NCH3, H-2), 2.65 (dd, 1H, J 9.4 Hz, J 3.7 Hz,H-20), 2.58 (dd, 1H, J 9.9 Hz, J 6.6 Hz, H-50), 2.14e2.08 (m, 1H, H-9), 2.00 (dtt, 1H, J 12.9 Hz, J 6.5 Hz, J 3.3 Hz, H-10), 1.90e1.78(m, 2H, H-11, H-12), 1.68e1.59 (m, 1H, H-120), 1.48 (dt, 1H,J 13.5 Hz, J 6.7 Hz, H-15), 1.38 (dd, 1H, J 12.1 Hz, J 3.2 Hz, H-13), 1.18 (t, 1H, J 12.3 Hz, H-90), 0.95e0.85 (m, 10H, H-11?, H-14, H-16). 13C NMR (100 MHz, CDCl3) d 172.8 (C]O), 138.9 (C-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). HR-ESI-QToF MS (positivemode): m/z calcd for C24H36N3O2 [MH]: 398.2802, found:398.2806.

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, Step 1 : To an ice-cooled solution of 26a (4.77g, 30mmol), 98% H2SO4 (1.95mL), H2O (4.5mL) and acetone (3OmL) was added 85% mCPBA (7.9 Ig, 39mmol) with stirring. The mixture was allowed to react for 48hrs at r.t. Acetone was evaporated and the mixture was neutralized with IN aq. NaOH and extracted with toluene. The organic phase was dried over anhy. MgSO4 and evaporated. The residue was purified by column chromatography (EArPE=I :4) to provide 26b (2.Og, 38%).

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

Reference£º
Patent; XCOVERY, INC.; WO2008/33562; (2008); A2;,
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.

General Procedure for the synthesis of Pauson-Khand adducts. To a solution of the acetylene (1.1 eq) (of general formula III (see above)) 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) (of general formula II (see above and different examples 0 below)) 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, 1H), 2.37 (t, J=9Hz, 1H). 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+)., 6913-92-4

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

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