Downstream synthetic route of 39514-19-7

39514-19-7 Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate 419705, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.39514-19-7,Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

Step A. 3-Oxo-piperidine-1 ,4-dicarboxylic acid 1 -tert-butyl ester 4-ethyl ester. A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman’s catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H)., 39514-19-7

39514-19-7 Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate 419705, apiperidines compound, is more and more widely used in various fields.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
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Simple exploration of 39514-19-7

The synthetic route of 39514-19-7 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.39514-19-7,Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

Example 35(+/-)-cis-3-Butyl-4-(4-cyclohexyloxy-phenyl)-6-(3-methoxy-1-methyl-piperidin-4-ylmethoxy)-pyridazine dihydrochlorideTo a stirred suspension of 1 -benzyl -3-oxo-pi peri di n e-4-carboxyl i c acid ethyl ester hydrochloride salt (25 g) in EtOAc (500 mL) was added saturated sodium bicarbonate solution (200 mL) and continued stirring for 2 h. The organic layer was separated, dried over Na2S04, filtered and concentrated to provide ethyl 1 -benzyl-3-oxo-pi peri di ne-4-carboxyl ic acid ethyl ester (22.00 g). To a solution of ethyl 1-benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (22 g, 84.18 mmol) in EtOAc (75 mL) was added (Boc)20 (20.21 g, 92.59 mmol) followed by 10percent Pd-C (2.4 g) and the resultant reaction mixture was subjected to hydrogenation at 50 psi of hydrogen for 14 h. The catalyst was filtered by passing through a pad of celite, washed the celite pad with EtOAc (200 mL) and the combined filtrate was concentrated. The residue was purified by flash silica gel column chromatography by eluting with 0.5percent ethyl acetate in hexanes to provide ethyl 3-oxo- pi peri di ne- 1 , 4-d i carboxyl i c acid 1-tert-butyl ester 4-ethyl ester (34 g)., 39514-19-7

The synthetic route of 39514-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

New learning discoveries about 39514-19-7

39514-19-7, 39514-19-7 Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate 419705, apiperidines compound, is more and more widely used in various fields.

39514-19-7, Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3 Alternative synthesis of (3R,37?,4 ‘S)-l’-(6-amino-5-fluoropyrimidin-4-yl)-3-((3-chloro-5- (trifluoromethyl) phenyl)amino)-2-oxo- [ 1 ,3 ‘-bipiperidine] -4 ‘-carboxamide. [0101] In addition to the methods described in Example 2, (3R,3’R,4’S)- -(6-amino-5- fluoropyrimidin-4-yl)-3-((3-chloro-5-(trifluoromethyl) phenyl)amino)-2-oxo-[ 1 ,3 ‘-bipiperidine] – 4’-carboxamide (compound 1-1) was also synthesized according to Scheme 6. Scheme 6 3-1 3-2 [0102] 1-tert- utyl 4-ethyl 3-oxopiperidine-l,4-dicarboxylate 3-2. To a solution of 3-1 (5.0 kg, 19.1 mol, 1.0 equiv) in EtOH (50 L) under N2 was added (Boc)20 (4.2 kg, 19.1 mol, 1.0 equiv), Et3N (1.9 kg, 19.1 mol, 1.0 equiv) and 10percent Pd(OH)2/C (250 g, 10percentw/w). After evacuated and refilled with hydrogenation three times, the mixture was stirred under 1 atm of hydrogen at 50 °C for 15 hr. LC-MS indicated completely consumption of 3-1. After the mixture was cooled to ambient temperature, the catalyst was filtered through a layer of celite and washed with EtOH (2.5 L). The filtrate was concentrated in vacuo to afford crude 3-2 (5.2 kg) as an oil, which was used in next step without further purification.

39514-19-7, 39514-19-7 Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate 419705, apiperidines compound, is more and more widely used in various fields.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; CONLON, Patrick; CHAN, Timothy R.; JENKINS, Tracy J.; CAI, Xiongwei; HUMORA, Michael; SHI, Xianglin; MILLER, Ross A.; THOMPSON, Andrew; WO2013/185084; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Some tips on 39514-19-7

39514-19-7, The synthetic route of 39514-19-7 has been constantly updated, and we look forward to future research findings.

39514-19-7, Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman’s catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H).

39514-19-7, The synthetic route of 39514-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Analyzing the synthesis route of 39514-19-7

39514-19-7, As the paragraph descriping shows that 39514-19-7 is playing an increasingly important role.

39514-19-7, Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3A 3-Oxo-piperidine-1,4-dicarboxylic Acid 1-tert-butyl Ester 4-ethyl Ester A mixture of commercially available ethyl-N-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (Aldrich, 75.4 g, 0.25 mol), di-t-butyl dicarbonate (58.5 g, 0.27 mol), Et3N (36 mL, 0.26 mol), and Pd(OH)2/C (7.5 g, 50percent in H2O) in 660 mL EtOH was put under 60 psi of H2 and was shaken for 25 min. The mixture was then filtered and the filtrate was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. MS (DCl/NH3) m/z 272 (M+H)+.

39514-19-7, As the paragraph descriping shows that 39514-19-7 is playing an increasingly important role.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Brief introduction of 39514-19-7

As the paragraph descriping shows that 39514-19-7 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.39514-19-7,Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

STEP A: l -Benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (5.0 g, 16.8 mmol) was stirred in dry ethanol (55 mL). The flask was evacuated and filled with nitrogen prior to the addition of 10percent Pd/C ( 1 .0 g). The resulting suspension was stirred for 16 hours under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated to afford a yellow solid (2.9 g). This was immediately dissolved in CH2C12 (100 mL), treated with Boc-anhydride (4.4 g, 20.2 mmol) and DIPEA (4.3 g, 33.6 mmol), and stirred for 16 hours at room temperature. The organics were washed sequentially with HCI (IN), water and brine, dried over magnesium sulfate, filtered, and concentrated to afford 3-oxo-piperidine-l ,4-dicarboxylic acid 1 -te -butyl ester 4-ethyl ester as a clear oil (4.8 g, 100percent yield). MS (ESI) m/e (M+H+): 271.36, 39514-19-7

As the paragraph descriping shows that 39514-19-7 is playing an increasingly important role.

Reference:
Patent; NOVARTIS AG; MILLER-MOSLIN, Karen; TOURE, Bakary-Barry; VISSER, Michael Scott; YUSUFF, Naeem; WO2011/29842; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem