Category: 872-32-2

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;,
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

General procedure: A mixture of 2-methyl-1-pyrroline (2.8 g, 33.7 mmol) and the corresponding cyclic phosphite 2a-2e (30.6 mmol) were stirred in toluene (5 mL) for 4-6 h at room temperature (conversion was checked by TLC or 31P NMR), the mixture was poured into 30 mL water, slowly acidified to pH 3 with 11 N HCl then quickly extracted with tert-butyl methyl ether (TBME) (3 .x. 20 mL). The aqueous phase was basified to pH 9-10 with NaOH pellets then extracted with CH2Cl2 (4 .x. 20 mL). The combined organic phases were dried over MgSO4, filtered and roto-evaporated to give the crude aminophosphonates 3a-3e as white powders which were then purified by SiO2 column chromatography with eluent CH2Cl2/EtOH 8/1.

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

Reference£º
Article; Gosset, Gae?lle; Cle?ment, Jean-Louis; Culcasi, Marcel; Rockenbauer, Antal; Pietri, Sylvia; Bioorganic and Medicinal Chemistry; vol. 19; 7; (2011); p. 2218 – 2230;,
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, 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.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

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.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.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).

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

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

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, General procedure: A mixture of 2-methyl-1-pyrroline (2.8 g, 33.7 mmol) and the corresponding cyclic phosphite 2a-2e (30.6 mmol) were stirred in toluene (5 mL) for 4-6 h at room temperature (conversion was checked by TLC or 31P NMR), the mixture was poured into 30 mL water, slowly acidified to pH 3 with 11 N HCl then quickly extracted with tert-butyl methyl ether (TBME) (3 .x. 20 mL). The aqueous phase was basified to pH 9-10 with NaOH pellets then extracted with CH2Cl2 (4 .x. 20 mL). The combined organic phases were dried over MgSO4, filtered and roto-evaporated to give the crude aminophosphonates 3a-3e as white powders which were then purified by SiO2 column chromatography with eluent CH2Cl2/EtOH 8/1.

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

Reference£º
Article; Gosset, Gae?lle; Cle?ment, Jean-Louis; Culcasi, Marcel; Rockenbauer, Antal; Pietri, Sylvia; Bioorganic and Medicinal Chemistry; vol. 19; 7; (2011); p. 2218 – 2230;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

872-32-2,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.

At 55 – 60 ¡ãC with vigorous stirring to a mixture of NCS (107 g, 800 mmol) in THF (250 mL) in a 2 L flask was added 5-methyl-3,4-dihydro-2H-pyrrole (8.3 g, 100 mmol) in one- portion. After addition, the reaction spontaneously heated to reflux for about 5 min, then reacted at 60 – 70 ¡ãC for another 1.5 hours. After cooled to r.t., hexane (300 mL) and water (300 mL) were added to the mixture. The organic layer was separated, collected and concentrated. The residue was used in the next step without further purification.

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

Reference£º
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15523; (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, General procedure: Acyl chloride (1.2 mmol, 1.2 equiv) was added to a solution of 4-dimethylaminopyridine (DMAP) (1.2 mmol, 1.2 equiv) in acetonitrile (1.0 mL) at 0 ¡ãC. The reaction was stirred at room temperature for 15 min. A solution of the 5-methyl-3,4-dihydro-2H-pyrrole (1.0 mmol) in acetonitrile (1.0 mL) was added and the reaction was stirred at room temperature for 3 h. p-Toluenesulfonic acid monohydrate (3.0 mmol, 3.0 equiv) was added at 0 ¡ãC under inert atmosphere. The reaction was then stirred at room temperature for 2 h. Arylhydrazine (1.5 mmol, 1.5 equiv) was added and stirred for an addition 5 min at room temperature. The reaction was then heated to 82 ¡ãC for 20 h. The reaction cools down to room temperature. The residue was then dissolved in ethyl acetate and washed with brine and a saturated aqueous solution of NaHCO3. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude solid, which was purified by column chromatography on silica gel.

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

Reference£º
Article; Yeo, Se Jeong; Liu, Yongxiang; Wang, Xiang; Tetrahedron; vol. 68; 3; (2012); p. 813 – 818;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem