Heterocyclic Building Blocks-Pyrrolines

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.

[4708] 6 mg (7.12 f.tmol) of this intermediate were taken upin 1 ml of dioxane and then admixed with 6.6 mg (42.7 flillOI)of methyl 2,5-dioxo-2,5-dihydro-lH-pyrrole-1-carboxylateand with 5 fll of saturated aqueous sodium hydrogencarbonatesolution. The reaction mixture was stirred at RT for 1 h.Then another 3 portions each of 50 fll of the saturated aqueoussodium hydrogencarbonate solution were added, and thereaction mixture was stirred at RT for another 30 min. Thenthe reaction mixture was acidified to pH 2 with trifluoroaceticacid and subsequently concentrated in vacuo. The remainingresidue was purified by means of preparative HPLC. Afterlyophilization from acetonitrile/water, 4 mg (60% of theory)of the title compound were obtained as a foam.[4709] HPLC (Method 12): R,=l.9 min;[4710] LC-MS (Method 11): R,=0.88 min; MS (ESipos):mz=923 (M+Hr.

55750-48-6, 55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; SEATTLE GENETICS, INC.; LERCHEN, Hans-Georg; LINDEN, Lars; SHEIKH, Sherif El; WILLUDA, Joerg; KOPITZ, Charlotte C.; SCHUHMACHER, Joachim; GREVEN, Simone; MAHLERT, Christoph; STELTE-LUDWIG, Beatrix; GOLFIER, Sven; BEIER, Rudolf; HEISLER, Iring; HARRENGA, Axel; THIERAUCH, Karl-Heinz; BRUDER, Sandra; PETRUL, Heike; JOeRISSEN, Hannah; BORKOWSKI, Sandra; US2015/246136; (2015); A1;,
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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

Part A: Phenylmethyl (cis)-3,4-dihydroxy-1 -pyrrolidinecarboxylate. Phenylmethyl 2,5-dihydro-1/-/-pyrrole-1-carboxylate (commerically-available) (5.07 g, 25 mmol) was dissolved in a mixture of acetone (25 mL) and water (10 ml_). NMO (5.9 g, 50 mmol) was added followed by catalytic OsO4. The reaction was stirred for 19 hours and then quenched by the addition of an aqueous solution of Na2S2psi3. A standard workup followed by silica gel chromatography (3:1 Hexane:ethyl acetate to pure ethyl acetate to 9:1 DCM: MeOH) yielded phenylmethyl (cis)-3,4-dihydroxy-1-pyrrolidinecarboxylate (0.872 g, 15percent) as a clear oil. LCMS: (M+H)+: 237.9.

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; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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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, Intermediate (i) 2-Methyl-[1 ,3′]bipyrrolidinyl-1 ‘-carboxylic acid tert-butyl esterTo a solution of N-BOC-3-pyrrolidinone (4.22g, 22.9 mmol) and 2- methylpyrroline (1.95 g, 22.9 mmol) (HCI salt was made by addition of 22.9 mL of 1 M HCI in ether into the DCM solution of 2-methylpyrroline, then evaporated) in DCE (60 ml_) was added powdered sodium triacetoxyborohydride slowly under N2 at r.t. The yellowish milky solution was stirred at r.t. overnight. LC/MS – m/z 255 and 199 (base and M-tBu).The reaction was quenched with aq. NaHCO3 solution (100 ml_). The two layers were separated, and the aqueous layer was extracted with DCM (20 ml_ x 2). The combined DCM extracts were washed with sodium bicarbonate (10 ml_), and brine (5 ml_x2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with DCM and 7.5percent MeOH in DCM to get 5.50 g (yield: 94percent) of the title compound as a liquid. MS: 255 (M+H+); TLC: 0.5 (10percent MeOH in DCM).

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

Reference£º
Patent; SANOFI-AVENTIS; GAO, Zhongli; HARTUNG, Ryan; STEFANY, David; WO2010/65798; (2010); A1;,
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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.

n-Butyllithium (53.0 mL, 133 mmol, 2.5 M solution in hexanes) was added dropwise to a stirred solution of diisopropylamine (18.6 mL, 133 mmol) in THF (120 mL) at 0 C. After 5 min, the solution was cooled to -78 C and a solution of 2-methyl-1-pyrroline (11.4 mL, 120 mmol) in THF (120 mL) was added dropwise. The reaction mixture was stirred at -78 C for 2 h. A solution of 1-bromo-3-chloropropane (12.5 mL, 126 mmol) in THF (120 mL) was then added dropwise and the mixture was stirred at RT for 16 h. The mixture was poured into 0.5 M aq. NaOH solution (450 mL), the product extracted into ether (3 * 500 mL), and the combined organic extracts were dried over K2CO3, filtered and concentrated in vacuo to afford 2,3,5,6,7,8-hexahydro-1H-indolizin-4-ium chloride as a yellow-orange solid (18.0 g, 94%). Rf 0.65 (100:10:1 CHCl3:MeOH:aq. NH3 (18 M)); numax (thin film)/cm-1 3396w, 2950s, 2867 m, 1644s, 1431 m, 1303 m, 1015w; deltaH (400 MHz, C6D6) 1.38 – 1.61 (6 H, m), 1.89 – 2.00 (4 H, m), 3.12 (2 H, t, J 6.5), 3.73 (2 H, app. tquin, J 7.5, 5.5, 2.0); deltaC (100 MHz, C6D6) 22.8, 23.7, 32.5, 32.7, 37.3, 44.8, 61.3, 175.5; m/z (ESI+) 162 (M(37Cl)H+, 32%), 160 (M(35Cl)H+, 100), 124 ((M – Cl)+, 35). To a stirred solution of the iminium salt (9.00 g, 56.4 mmol) in water (900 mL) was added powdered NaOH (56.4 g, 1.41 mol) and the reaction mixture was stirred at RT for 16 h. Pentane (900 mL) was added and the mixture was stirred at RT for 1 h. The separated organic layer was dried over K2CO3, filtered and concentrated in vacuo to afford the title compound as a colourless oil (5.15 g, 74%). numax (thin film)/cm-1 2930s, 1683 m, 1648w, 1445w, 1280m, 1185 m; deltaH (400 MHz, C6D6) 1.47 – 1.56 (2 H, m), 1.81 – 1.88 (2 H, m), 2.12 – 2.18 (2 H, m), 2.24 – 2.31 (2 H, m), 2.66 (2 H, t, J 6.5), 2.80 (2 H, t, J 5.5), 4.43 (1 H, tt, J 3.5, 1.5); deltaC (100 MHz, C6D6) 21.9, 22.4, 23.5, 29.2, 47.1, 53.1, 88.2 (4 carbon not observed); m/z (ESI+) 124 (MH+, 100%)., 872-32-2

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

Reference£º
Article; Seah, Kang Yee; Robertson, Jeremy; Tetrahedron; vol. 75; 46; (2019);,
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, A mixture of N-Boc-ethylenediamine (5.6 mL, 35.4 mmol, 1.1 eq. ) and saturated NaHCO3(60 mL) was cooled to 0 , to which compound 409 (5.00 g, 32.2 mmol, 1.0 eq. ) was added in portions. After stirring at 0 for 30 min, the reaction was warmed to r.t. and stirred for 1 h. The precipitate was collected by filtration and washed with cold water, then dissolved in EtOAc and washed with brine, dried over anhydrous Na2SO4and concentrated to give a white solid (6.69 g, 87%yield) .

55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
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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 1: t-Butyl (2-(2-(2-aminoethoxy)ethoxy)ethyl)carbamate(250 mg, 1.0 mmol) andmethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate (156 mg, 1.0 mmol) were combined in saturated aqueous NaHCO3 (10 ml) and stirred for 1.5 h at 0C. The reaction mixture was acidified to pH 2 with hydrochloric acid (2 M) and extracted with EtOAc. The organic phase was washed with brine, dried with MgSO4, and concentrated. The crude was purified by ISCO using 0-4% MeOH/DCM to give t-butyl (2- (2-(2-(2,5 -dioxo-2,5 -dihydro- 1 H-pyrrol- 1 -yl)ethoxy)ethoxy)ethyl)carbamate as a colorless oil. MS m/z 229.2(M+1-Boc). Retention time 0.963 mm. ?H NMR (400 MHz, Chloroform-d) 6 6.71 (s, 2H), 5.04 (bs,1H), 3.74 (t, J = 5.4 Hz, 2H), 3.64 (t, J = 5.4 Hz, 2H), 3.61-3.59 (m, 2H), 3.56-3.54 (m, 2H), 3.50 (t, J =5.2 Hz, 2H), 3.31-3.26(m, 2H), 1.44 (s, 9H).

55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; ABRAMS, Tinya; COHEN, Steven; D’ALESSIO, Joseph Anthony; DAMIANO, Jason; DURR, Clemens; GEIERSTANGER, Bernhard Hubert; HU, Qi-Ying; HUBER, Thomas; IMASE, Hidetomo; JIN, Yunho; MENEZES, Daniel; MILLER, Kathy; MOHSENI, Morvarid; OU, Weijia; RENDAHL, Katherine; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; (350 pag.)WO2016/203432; (2016); 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, A solution of 5-methyl-3,4-dihydro-2H-pyrrole (83 mg, 1.0 mmol), allyl chloride (114 mg, 1.5 mmol), Pd(AcO)2 (4 mg, 0.02 mmol), PPh3 (21 mg, 0.08 mmol), and Et3N (202 mg, 2.0 mmol) in THF (15 mL) was placed in a 45 mL autoclave. The autoclave was purged, pressurized (400 psi CO) and then heated at 100 ¡ãC, under magnetic stirring, for 4 h. After this time, the solution was cooled to room temperature and the solvent was removed under reduced pressure to give a crude material. The crude mixture was then purified by flash chromatography (silica gel, partly deactivated with triethylamine, eluent petroleum ether/ethyl acetate 70:30) to afford the pure beta-lactam 2 as a pale yellow oil (121 mg, 80percent). 1H NMR (400.13 MHz, CDCl3): delta 2.23 (3H, s, CH3), 2.44-2.56 (2H, m, CH2CH2CH2), 3.04-3.15 (2H, m, CH2CH2CH2N), 3.79-3.92 (2H, m, CH2N), 4.81 (1H, d, J=6.0 Hz, CHC=O), 5.13-5.20 (2H, m, CH=CH2), 5.94-6.02 (1H, m, CH=CH2) ppm. 13C NMR (100.62 MHz, CDCl3): delta 16.4 (2C, CH3 and CH2CH2CH2), 27.2, 41.1, 48.1, 74.1, 117.8, 131.3, 168.8 ppm. FT-IR (CHCl3): nu=3083, 2981, 2929, 2866, 1670, 1632, 1416 cm-1. GC-MS (70 eV): m/z (percent)=151 (33) [M]+, 110 (9), 83 (80), 82 (100), 68 (20). HRMS (ESI): calcd for C9H14NO [M+H]+ 152.1076; found 152.1078.

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

Reference£º
Article; Perrone, Serena; Cannazza, Giuseppe; Caroli, Antonio; Salomone, Antonio; Troisi, Luigino; Tetrahedron; vol. 70; 39; (2014); p. 6938 – 6943;,
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.5264-35-7,5-Methoxy-3,4-dihydro-2H-pyrrole,as a common compound, the synthetic route is as follows.

5264-35-7, EXAMPLE I 5-Amino-2,3-dihydro-1H-indolizin-7-one Monohydrochloride To a solution of lithium diisopropylamide (LDA), prepared from n-BuLi (125 ml, 0.2M) and diisopropylamine (20.24 g, 0.2M), in dry THF (200 ml) was added under N2 at -10¡ã C. 5-methylisoxazole (8.31 g, 0.1 M). The resultant yellow suspension was stirred at -10¡ã C. for 1 hr before 1-aza-2- methoxy-1-cyclopentene (9.9 g, 0.1M) was added dropwise. A light yellow precipitate was immediately formed. The mixture was allowed to warm to ambient over a period of 19 hr. MeOH (100 ml) was slowly added with external cooling so that the internal temperature remained at 25¡ã-26¡ã C. The resulting reddish solution was then stirred at ambient for 24 hr and evaporated in vacuo. Flash column chromatography (30percent MeOH in CH2 Cl2 on silica gel, Em-60) followed by recrystallization (MeOH/Et2 O) gave the desired free base (3 g, 20percent); mp> 230¡ã C. It was then transformed into its HCl salt in MeOH with conc HCl. The salt was further recrystallized from MeOH/Et2 O to yield the title compound; mp>250¡ã C. yield 3 g, 81percent); TLC (30percent MeOH in CH2 Cl2); Rf=0.37; IR (KBr) cm-1, 3500, 3140, 1670, 1590. Anal. Calcd for C8 H10 N2 O. HCl: C, 51.48; H, 5.94; N, 15.01. Found: C, 51.08; H, 5.77; N, 14.89.

The synthetic route of 5264-35-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ortho Pharmaceutical Corporation; US4602013; (1986); A;,
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

General procedure: 2-Methyl-pyrroline (1equiv.) was added to a suspension of an enzyme (20% weight) in a mixture of toluene/water (20mL/100muL), followed by the addition of benzylamine (1equiv.) and isocyanoester 1 (1equiv.). The mixture was stirred at room temperature. The enzyme and water were filtered off through a funnel containing Celite and MgSO4. The solvent was then evaporated in vacuum. The product was purified by column chromatography (silica gel, DCM/methanol).

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

Reference£º
Article; Wilk, Monika; Brodzka, Anna; Koszelewski, Dominik; Madej, Arleta; Paprocki, Daniel; ??d?o-Dobrowolska, Anna; Ostaszewski, Ryszard; Bioorganic Chemistry; vol. 93; (2019);,
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.31970-04-4,Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of benzyl 2,5-dihydro-l H-pyrrole-l -carboxylate (2.00 g, 9.80 mmol) in CH2C12 (10 mL) was added slowly 3-chloroperbenzoic acid (3.00 g, 14.80 mmol) at 0 ¡ãC. The reaction mixture was stirred for 13 h at room temperature, then quenched with saturated sodium thiosulfate aqueous solution and extracted with EtOAc. The organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 6: 1 (v/v) PE/EtOAc) to give the title compound as colorless oil (1.75 g, 81.02 percent)., 31970-04-4

As the paragraph descriping shows that 31970-04-4 is playing an increasingly important role.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyrroline – Wikipedia
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