Heterocyclic Building Blocks-Pyrrolines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31970-04-4,Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

Benzyl 6-oxa-3-azabicvclo[3.1.Olhexane-3-carboxylate z To a solution of benzyl 2,5-dihydro-1 H-pyrrole-1-carboxylate (33 g, 163 mmol; 90% from Aldrich) in dichloromethane (540 ml_, 0.3 M solution) was added m-CPBA (44 g, 340 mmol, 77% from Aldrich). After the reaction mixture was stirred at room temperature for 18 h, 500 ml_ of saturated Na2C03 aqueous solution was added and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated, washed with water and brine, dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The desired product as a yellow oil was obtained in 83% yield (29.5 g) by flash column chromatography. Rf = 0.5 (30% EtOAc in hexanes). 1H NMR (CDCI3, 400 MHz): delta 3.38 (2H, dd, J = 12.8, 6.0 Hz ), 3.68 (2H, d, J = 3.6 Hz), 3.87 (2H, dd, J = 13.2, 19.6), 5.1 1 (2H, s), 7.33( 5H, m). LC/MS (uplc): MH+ 220.0, 0.69 min., 31970-04-4

The synthetic route of 31970-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; IRM LLC; BARSANTI, Paul A.; CHAMOIN, Sylvie; DOUMAMPOUOM-METOUL, Lionel; GEIERSTANGER, Bernhard Hubert; GROTZFELD, Robert Martin; GUERRO-LAGASSE, Stephanie; JONES, Darryl Brynley; KARPOV, Alexei; LAFRANCE, Marc; NIETO-OBERHUBER, Cristina; OU, Weijia; PIIZZI, Grazia; WO2014/151030; (2014); 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.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.

872-32-2, To a solution of i-Pr2NH (1.52 g, 2.1 mL, 15 mmol, 1.5 equiv) in anhyd THF (20 mL) was added n-BuLi (6 mL, 15 mmol, 1.5 equiv, 2.5 M in hexane) via a syringe at 0 ¡ãC under a nitrogen atmosphere, and the resulting solution was stirred for 30 min at 0 ¡ãC. Subsequently, 2-methyl-1-pyrroline (1; 0.83 g, 0.95 mL, 10 mmol, 1 equiv) was added via a syringe at 0 ¡ãC and the resulting solution was stirred for 1 h at 0 ¡ãC. Then, a solution of 1-benzyl-2-(bromomethyl)aziridine (2, R = Ph;8 2.25 g, 10 mmol, 1 equiv) in THF (10 mL) was added via a syringe at 0 ¡ãC and the resulting solution was stirred for 17 h at r.t. Afterwards, the reaction mixture was poured into H2O (50 mL) and extracted with Et2O (3 ¡Á 50 mL). Drying (MgSO4), filtration of the drying agent, and evaporation of the solvent in vacuo furnished 3a as an orange oil; yield: 2.12 g (9.3 mmol, 93percent). Because of the high purity of the obtained aziridines 3 (purity >95percent, 1H NMR), these compounds were used as such in the next step. IR (film): 2922, 1643, 1452, 732, 698 cm?1. 1H NMR (400 MHz, CDCl3): delta = 7.24?7.33 (m, 5 H), 3.75?3.80 (m, 2 H), 3.52 (d, J = 13.1 Hz, 1 H), 3.25 (d, J = 13.1 Hz, 1 H), 2.26?2.37 (m, 4 H), 1.78?1.87 (m, 3 H), 1.65 (d, J = 3.2 Hz, 1 H), 1.52?1.61 (m, 2 H), 1.43 (d, J = 6.2 Hz, 1 H). 13C NMR (100 MHz, CDCl3): delta = 177.7, 139.4, 128.31 (2 C), 128.28 (2 C), 127.0, 65.0, 60.8, 39.1, 37.3, 34.2, 31.4, 29.6, 22.5. MS (70 eV): m/z (percent) = 229 (M+ + 1, 100). HRMS (ESI): m/z calcd for C15H21N2: 229.1699 [M + H]+; found: 229.1703.

872-32-2 2-Methyl-1-pyrroline 70103, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Article; Dolfen, Jeroen; D?hooghe, Matthias; Synthesis; vol. 49; 10; (2017); p. 2215 – 2222;,
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.55750-48-6,Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

55750-48-6, Step 1t-Butyl (2-(2-aminoethoxy)ethyl)carbamate (204 mg, 1 mmol) was dissolved in saturated aq. NaHCO3 (1 0 mL). The solution was cooled to 0 C. Methyl-2,5-dioxo-2,5- dihydro-1 H-pyrrole-1 -carboxylate (155 mg, 1.0 mmol) was then added. The reaction was stirred for 1 .5 h at 0 C. The pH was adjusted to 1 -2 with 2M HCl, and the mixture was extracted with EtOAc (3 X 20 mL). The combined organic phases was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO using a 0-4% gradient of MeOH in DCM to obtain tert-butyl (2-(2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol- 1 -yl)ethoxy)ethyl)carbamate. 1H NMR (400 MHz, CD3OD): 6.82 (s, 2H), 3.68 (t, J = 5.4 Hz, 2H), 3.59 (t, J = 5.4 Hz, 2H), 3.46 (t, J = 5.6 Hz, 2H), 3.1 8-3.14 (m, 2H), 1.43 (s, 9H). MS m/z 1 85.1 (M+1 -Boc). Retention time 0.918 min.

As the paragraph descriping shows that 55750-48-6 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; PAN, Shifeng; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; WO2015/189791; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

55750-48-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55750-48-6,Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

A solution of amine 8 (23.9 mg, 29. 0 [JMOL)] dissolved in 1 M aqueous solution of NaHCO3 (1 mL) was treated with methoxycarbonylmaleimide (27.03 mg, 17. [4] pmol) at [0 C.] After 5 min, the mixture was diluted with water (1 [ML)] and acetonitrile (2 mL), and then stirred at room temperature for 1 h. The mixture was diluted with CH2Cl2 (50 mL) and washed with brine [(3X10] mL). The organic phase was dried over [NA2SO4,] filtered and concentrated. The oily residue was purified by flash chromatography [(CH2CL2/MEOH] 96: 4) to give maleimide 9 (20.3 mg, 71%) ; Rf 0. 45 [(CH2CL2/MEOH] 96: 4) [;’H-NMR (CDC13/TMS)] : [No.6. ]72 (s, 8 H, CH=CH), 4.94 (d, [1] H, J=3. 4 Hz, [H-1),] 3.95-3. 82 (m, 2 H, H-4, and [OCHHCH2CH2N),] 3. [80No.3. ]45 (m, 22 H, H-2, H-3, H-5, H-6, H-6′, [OCH2CH2CH2S,] SCH2CH2N, and [OCH2CH3),] 2.90-2. 60 (m, 16 H, [OCH2CH2CH2SCH2CH2N),] 1.96-1. 82 (m, 8 H, OCH2CH2CH2S), 1.23 (t, 3 H, J=7.1 Hz, OCH2CH3) ; ES-MS: 1019.49 (M+Na) [+,] 951 (M-OEt) +.

As the paragraph descriping shows that 55750-48-6 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE; WO2004/802; (2003); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

872-32-2, 2-Methyl-1-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

872-32-2, To an ice-cooled mixture of Compound I (5.0 g) and THF (150 mL) was added NCS (64.2 g), and the mixture was stirred at 55¡ãC for 1 hour. To the reaction mixture was added water, and the mixture was extracted with hexane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give Compound II.

872-32-2 2-Methyl-1-pyrroline 70103, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

31970-04-4, Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[BENZYL-3-PYRROLINE-1-CARBOXYLATE] (5 g, 24.6 mmol) and 3-chloroperoxybenzoic acid (8.5 g, 49.2 mmol) were dissolved in dichloromethane (250 [ML)] and stirred for 16 h at room temperature. The reaction mixture was washed with sat. [NAHC03,] brine and dried [(MGS04).] The title compound was isolated by silica gel chromatography (0-35% EtOAc-hexanes). Yield 3.6 g (68%). [1H NMR] (300 MHz, [CDC13)] : 3.34-3. 40 (d, [J=] 11 Hz, 2H), 3.66 (s, 2H), 3.80- 3.89 (t, [J=] 12 Hz, 2H), 5. [10] (s, 2H), 7.27-7. [38] (m, [5H).]

31970-04-4, The synthetic route of 31970-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/33451; (2004); 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.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.

872-32-2, 5-Methyl-3,4-dihydro-2H-pyrrole (1.00 g, 12.0 mmol) was dissolved in carbon tetrachloride. To the solution was added NCS (12.85 g, 96 mmol) as a solid and reaction mixture heated to 85 0C and stirred overnight. The mixture was cooled to 0 0C and the precipitate filtered off and the solvent evaporated. The residue was dissolved in methanol and sodium methoxide (3.90 g, 72.2 mmol) was added. The resulting suspension was heated to reflux and stirred for 3 h. The methanol was evaporated and the residue suspended in Et20. The solid was filtered off and the ether evaporated. The residue was dissolved in DCM and 2M HCI was added. The biphasic solution was stirred until no SM remained. The phases were separated and the organic layer was dried over MgSO4 and evaporated to an orange oil. The crude oil was adsorbed onto silica and run on 40 g of silica with EtOAc and Hexanes to afford the title compound as an orange solid (0.2958 g, 1.854 mmol, 15.41 percent yield). 1H NMR (400 MHz, CDCI3): delta ppm 9.54 (br. s., 1 H), 6.80 (s., 1 H), 6.17 (s., 1 H), 3.83 (s, 3 H). MS: m/z 160.0 (M+1 ).

As the paragraph descriping shows that 872-32-2 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

5264-35-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5264-35-7,5-Methoxy-3,4-dihydro-2H-pyrrole,as a common compound, the synthetic route is as follows.

To a flask containing 18-1 (2.87 g, 28.9 mmol) at room temperature, diethyl 1,3-acetonedicarboxylate (7.90 mL, 43.4 mmol) and triethylamine (0.45 mL, 3.2 mmol) were added. The mixture was stirred at room temperature overnight then was heated to 35¡ã C. for 3 days. The mixture was cooled to room temperature and diluted with ether. The resulting suspension was filtered, washing with ether. Additional solid precipitated from the filtrate which was collected by filtration. The combined solids were dried under vacuum to give ethyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (18-2, 2.52 g) as a white solid.

As the paragraph descriping shows that 5264-35-7 is playing an increasingly important role.

Reference£º
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

55750-48-6, Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,55750-48-6

0-(P-D-glucopyranos-1 -yl)decyl-maleimide (38) N-(methoxycarbonyl) maleimide(37) (0.014 g, 0.09 mmol) was added at RT to a stirring solution of (10-Aminodecyl) p-D-glucopyranoside(0.015 g, 0.04 mmol) in dioxane (0.75 ml_) and sat. NaHC03 (aq) (1.5 ml_). The reaction was stirred for 1 hr after which the reaction was quenched with EtOAc (10 ml_) and water (10 mL). The organic phase was separated out and the aq. phase extracted with EtOAc (3 x 10 mL). The organic layers were combined, dried, filtered and the solvent evaporated under vacuum. The residue was adsorbed onto silica and purified with column chromatography (CH2CI2: MeOH 9: 1 ). The title compound was obtained as a clear oil (0.01 1 g, 60 %) Rf = 0.15 (CH2CI2: MeOH 9:1 ) deltaEta (CD3OD, 300 MHz): 6.79 (2H, s, 374′), 4.24 (1 H, d, J = 7.5 Hz, H-1 “), 3.93-3.84 (2H, m, H-6″a/H-10a), 3.69-3.64 (1 H, m, H-6″b), 3.57-3.50 (1 H, dt, J = 6.6, 9.6 Hz, H-10b), 3.48 (2H, t, J = 6.9 Hz, H-1 ), 3.38-3.22 (3H, m, H-3’74’75”), 3.19-3.13 (1 H, m, H-2″), 1.64-1 .54 (4H, m, H-2/9), 1.42-1 .28 (12H, m, AlkCHz). 5C (CD3OD, 100 MHz): 172.6 (C-275′), 135.3 (C-374′), 104.4 (C-1 “), 78.2 (C-3″), 77.9 (C-2″), 75.1 (C-5″), 71 .7 (C-10), 70.9 (C-4″), 62.8 (C-6”), 38.5 (C-1 ), 30.8 (C-2), 30.5 (x3), 30.1 , 29.4, 27.7, 27.0 (CH2Alk)

The synthetic route of 55750-48-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE SOUTH AFRICAN NUCLEAR ENERGY CORPORATION LIMITED; UNIVERSITY OF CAPE TOWN; DRIVER, Cathryn Helena Stanford; ZEEVAART, Jan Rijn; PARKER, Mohamed Iqbal; HUNTER, Roger; (67 pag.)WO2016/46793; (2016); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

31970-04-4, Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(2) Benzyl 2,5-dihydropyrrole-1-carboxylate (25 g) was dissolved in chloroform (125 mL), and mCPBA (39 g) was slowly added with ice cooling. The mixture was stirred at room temperature for 1 day, then diluted with chloroform, and washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium hydrogencarbonate. The organic layer was dried with anhydrous sodium sulfate, then the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 8:2-1:99) to obtain benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (18 g). MS: ESI+ (m/z) 242 (M++Na)

31970-04-4, The synthetic route of 31970-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2003131; (2008); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem