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Analyzing the synthesis route of 31970-04-4

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

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

To a solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (2.00 g, 9.80 mmol) in CH2Cl2 (10 mL) was added slowly 3-chloroperbenzoic acid (3.00 g, 14.80 mmol) at 0¡ã C. 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 Na2SO4 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, 81.02percent)., 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; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Brief introduction of 31970-04-4

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

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.

EXAMPLE 2; Ci5-l-methyl-3 (9Z,12ZVocta^^; Benzyl 3,4-dihvdroxypyrrolidine-l-carboxylate (9): In a 500 mL RBF, the Cbz Pyrroline (15 gs 73.8 mmol) was dissolved in a mixture of 100 mL THF, 60 mL t-BuOH and 40 mL water for addition of the NMO (30.6 ml, 148 mmol) solution followed by the osmium tetraoxide (0.925 ml, 0.074 mmol) solution. Heated in a 70C oil bath. Solution slowly went from yellow to brown. After 2h, cooled to RT and added 50 mL 10percent aqueous NaHS03. Concentrated and partitioned between 100 mL brine and 100 mL EtOAc. Separated layers and extracted with 100 mL EtOAc. Dried over MgS04, filtered and concentrated to 22.3 g of thick yellow oil. Flash column chromatography from 50-100percent EtOAc in hexane provided compound 9. .H NMR (400 MHz, CDC13) 5 7.35 (m, 5H), 5.22 (s, 2H), 4.42 (m, 4H), 3.63 (m, 2H), 3.42 (m, 3H), 3.20 (m, IH)., 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; MERCK SHARP & DOHME CORP.; STANTON, Matthew, G.; BEUTNER, Gregory, L.; WO2012/61259; (2012); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Downstream synthetic route of 31970-04-4

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

Step 1: Benzyl cis-3,4-dihvdroxypyrrolidine-l-carboxylate (127)To a solution of compound 126 (3.0 g, 14.76 mmol) in a mixture of acetone and water (32 mL and 6 mL) was added N-methylmorpholine-N- oxide (2.25 g, 19.21 mmol) followed by the addition of osmium tetroxide solution (4percent aqueous, 0.7 mL). The yellow mixture was stirred at ambient temperature overnight. To this solution was added solid sodium metabisulfite (Na2S205, 5.0 g) and the mixture was stirred for 1 h. Acetone was removed from the reaction mixture by evaporation, and the solid obtained was suspended in ethyl acetate and filtered. The solid was dissolved in water, extracted with ethyl acetate and combined with the filtrate. The organic phase was washed with brine, dried (Na2S04) and evaporated to get the crude compound 127. This material was purified by flash chromatography using 1-8percent methanol /dichloromethane as eluent to isolate the pure product as a white solid (3.02 g, 86percent).1H NMR (CDC13, 300MHz) : delta ppm 7.39-7.26 (m, 5H), 5.11 (s, 2H), 4.28-4.20 (m, 2H), 3.65 (dd, J = 11.0, 5.5 Hz, 2H), 3.41 (dt, J = 11.0, 4.1 Hz, 2H), 2.61-2.58 (m, 2H). APCI+ = 238., 31970-04-4

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

Reference£º
Patent; ALNYLAM PHARMACEUTICALS, INC.; RAJEEV, Kallanthottathil, G.; MANOHARAN, Muthiah; JAYARAMAN, Muthusamy; MAIER, Martin; JAYAPRAKASH, Narayanannair, K.; BUTLER, David; WO2012/99755; (2012); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

New learning discoveries about 31970-04-4

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

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

Step I: Epoxidation of alkene[00146] To a solution of benzyl 2,5-dihydro- 1 H-pyrrole- 1 -carboxylate (33 g, 163 mmol) in dichloromethane (0.3 M solution) was added MCPBA (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. NMR (CDCl3j 400 MHz): delta 3.38 (2H, m ), 3.68 (2H, m), 3.87 (2H, m), 5.1 1 (2H, s), 7.33( 5H, m). LC/MS (uplc): MH+ 220.0, 0.69 min.

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

Reference£º
Patent; NOVARTIS AG; BARSANTI, Paul, A.; DING, Yu; HAN, Wooseok; WO2011/128388; (2011); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

New learning discoveries about 31970-04-4

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

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

To a solution of N-carbobenzoxy-3-pyrroline (1.00 g, 4.92 mmol, 1.0 eq) in acetone (20 mL) was added NMO (1.0 g, 7.38 mmol, 1.5 eq) followed by OsO4 (cat. 10 mg in 1 mL iPrOH). The mixture was stirred for 3 h. To this, saturated NaHSO3 aqueous solution (5 mL) was added, and the mixture was stirred for another 0.5 h. The organic phase was separated from the mixture, and the water phase was extracted with EtOAc (20 mL¡Á3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (EtOAc) to give the compound as colorless oil (1.16 g, 100percent).

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

Simple exploration of 31970-04-4

31970-04-4 Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate 643471, apyrrolines compound, is more and more widely used in various fields.

To a solution of benzyl 2,5-dihydro-lH-pyrrole-l-carboxylate (33 g, 163 mmol) in dichloromethane (540 mL) was added MCPBA (77 wt. , 44 g) and the reaction mixture was stirred at room temperature for 18 hrs. The mixture was diluted with saturated aqueous sodium carbonate solution (500 mL) and the resulting mixture was stirred at room temperature for 1 hr. The separated organic layer washed with water and brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel] providing benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (29.5 g) as a yellow oil. 1H NMR (400 MHz, chloroform-d) delta [ppm]: 3.38 (dd, J = 12.8, 6.0 Hz, 2 H), 3.68 (d, J = 3.6 Hz, 2 H), 3.87 (dd, J = 13.2, 19.6, 2 H), 5.11 (s, 2 H), 7.33 (m, 5 H). LCMS (m/z): 220.0 [M+H]+; Rt = 0.69 min., 31970-04-4

31970-04-4 Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate 643471, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2011/26904; (2011); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Simple exploration of 383127-22-8

383127-22-8, As the paragraph descriping shows that 383127-22-8 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.383127-22-8,2-(4-Bromophenyl)pyrrolidine,as a common compound, the synthetic route is as follows.

A mixture of 2-(4-bromophenyl)pyrrolidine (50.0 mg, 221 pmol, 1.00 equiv), di-/er/- butyl dicarbonate (57.9 mg, 265 pmol, 1.20 equiv) and dimethylaminopyridine (2.70 mg, 22.1 pmol, 0.10 equiv) in tetrahydrofuran (1.00 mL) was purged with nitrogen and then was stirred at 25 C for 2 h. The mixture was filtered and concentrated under reduced pressure. The resultant residue was purified by prep-TLC (Si02, petroleum ether/ethyl acetate = 10/1) to afford tert- butyl 2-(4-bromophenyl)pyrrolidine-l-carboxylate (55.0 mg, 163 pmol, 73.6% yield, 96.5% purity) as a yellow oil. LC-MS [M-55]: 272.1.

383127-22-8, As the paragraph descriping shows that 383127-22-8 is playing an increasingly important role.

Reference£º
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

Analyzing the synthesis route of 945217-60-7

The synthetic route of 945217-60-7 has been constantly updated, and we look forward to future research findings.

945217-60-7, (3R,4S)-rel-tert-Butyl 3,4-diaminopyrrolidine-1-carboxylate is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,945217-60-7

A vial was charged with 4-(2-(ethoxymethoxy)-6-fluorobenzoyl)benzoic acid (32 mg, 0.099 mmol), Et3N (14 mu, 0.099 mmol) and DMF (1 .0 mL) at room temperature. To this solution was then added HATU (38 mg, 0.099 mmol) and the mixture was stirred for 5 min. This solution was then added to a second vial containing a freshly prepared mixture of tert- butyl (3R,4S)-3,4-diaminopyrrolidine-1 -carboxylate (20 mg, 0.099 mmol) and HCI (4.0 M dioxane solution, 50 mu) in DMF (0.5 mL). The resulting solution was stirred at room temperature for 18 h to give tert-butyl (3R,4R)-3-amino-4-(4-(2-(ethoxymethoxy)-6- fluorobenzoyl)benzamido)pyrrolidine-1 -carboxylate which could be directly used in situ. To this solution was added isonicotinic acid (12 mg, 0.099 mmol), Et3N (42 mu, 0.298 mmol) and HATU (38 mg, 0.099 mmol). The mixture was stirred at room temperature for 1 h, then quenched with water and extracted with EtOAc. The organic portion was concentrated in vacuo and then redissolved in THF (1 .0 mL) and aqueous HCI (1 .0 M, 0.5 mL). The solution was warmed to 65C and stirred until the carbamate and acetal protecting groups were fully removed by LCMS. The solution was then purified via HPLC to give N-((3R,4R)-4-(4-(2- fluoro-6-hydroxybenzoyl)benzamido)pyrrolidin-3-yl)isonicotinamide as a formate salt. 1 H NMR (500 MHz, Methanol-^) delta 8.78 – 8.69 (m, 2H), 8.50 (s, 1 H), 7.97 (d, J = 7.3 Hz, 2H), 7.91 (d, J = 7.8 Hz, 2H), 7.82 (d, J = 4.5 Hz, 2H), 7.39 (d, J = 8.0 Hz, 1 H), 6.82 – 6.76 (m, 1 H), 6.72 (t, J = 9.0 Hz, 1 H), 4.73 – 4.65 (m, 2H), 3.75 (d, J = 1 1 .1 Hz, 2H), 3.32 (s, 2H). LCMS (ESI+) for C24H21 FN4O4 [M+H] expected = 449.16, found = 449.26.

The synthetic route of 945217-60-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF MIAMI; AL-ALI, Hassan; LEMMON, Vance; BIXBY, John; (103 pag.)WO2019/89729; (2019); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

Brief introduction of 114676-93-6

114676-93-6, The synthetic route of 114676-93-6 has been constantly updated, and we look forward to future research findings.

114676-93-6, (2R,4R)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Compound 10 (0.70 g, 3.48 mmol) and PPh3 (1.37 g, 5.22 mmol) in CH2Cl2 (7 mL) was added DEAD (0.91 mL, 5.22 mmol) at 4 C. [Zhao et al., Eur. J. Med. Chem. 2005, 40, 231]. The resulting mixture was stirred for 10 min and then 4-nitrobenzoic acid (1.62 g, 5.22 mmol) was added. This mixture was allowed to warm up to room temperature and stirred for 16 hours. The reaction mixture was quenched with 2 N NaOH solution and extracted with AcOEt. The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash column chromatography to give Compound 15 (0.885 g, 73%) as a pale yellow solid. Compound 15: 1H NMR (400 MHz, CDCl3): delta 1.38 (d, J=0.4 Hz, 3H), 1.48 (s, 9H), 1.96 (d, J=14.4 Hz, 1H), 2.47 (m, 1H), 3.64-3.83 (m, 2H), 4.11 (m, 1H), 5.55 (m, 1H), 8.21 (d, J=8.0 Hz, 2H), 8.31 (d, J=8.0 Hz, 2H).

114676-93-6, The synthetic route of 114676-93-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tanaka, Fujie; Barbas, Carlos F.; Zhang, Haile; US2007/117986; (2007); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

Analyzing the synthesis route of 50609-01-3

50609-01-3 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline 6493749, apyrrolidine compound, is more and more widely used in various fields.

50609-01-3,50609-01-3, 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound (9a) (0.89 g, 4.6 mmol), DMAP (0.24 g), and EDCI (1.46 g, 7.6 mmol) were added in sequence to a solution of (6) (1.16 g, 3.8 mmol) in anhydrous THF (100 mL). An excess of triethylamine (5 mL) was added dropwise and the mixture was stirred at room temperature for 8 h. Then the reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with HCl (1 M), brine, saturated NaHCO3 solution and dried over Na2SO4. After filtration and concentration of the organic phase, crude (10) (1.19 g, 65%) was obtained. To a solution of (10) (1.19 g, 2.47 mmol) in methanol (60 mL) was added Pd/C (0.20 g), stirred for 24 h at room temperature under the atmosphere of hydrogen. The mixture was filtered to remove Pd/C, and the residue was purified by column chromatography yielding (17a) (0.92 g, 95%) as a white solid.

50609-01-3 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline 6493749, apyrrolidine compound, is more and more widely used in various fields.

Reference£º
Article; Lu, Wen; Li, Pengfei; Shan, Yuanyuan; Su, Ping; Wang, Jinfeng; Shi, Yaling; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1044 – 1054;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem