Category: 61995-20-8

61995-20-8,61995-20-8, Benzyl 3-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of benzyl 3-oxopiperidine-1-carboxylate (28 g, 0.12 mol) and ethane-1,2-diol (16.8 mL, 0.3 mol) in toluene (300 mL) was added 4-methylbenzenesulfonic acid (2.3 g, 0.0 12 mol) in a flask equipped with a Dean-Stark trap. Then the reaction was heated to reflux overnight. After cooling to room temperature the mixture was washed with water (200 mL),satd.NaHCO3 (aq) (100 mL), water (100 mL) and brine (100 mL), and dried overNa2504.The solution was concentrated in vacuo to obtain a residue, which was purified by silica gel chromatography (PE:EtOAc= 3 :1) to provide benzyl 1,4-dioxa-7-azaspiro[4.Sjdecane-7- carboxylate. 1H NMR (400 MHz, DMSO-d6) = 7.44 – 7.27 (m, 5H), 5.08 (s, 2H), 3.95 – 3.79 (m, 4H), 3.43 – 3.29 (m, 4H), 1.73 – 1.65 (m, 2H), 1.64 – 1.55 (m, 2H) ppm.

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph; KIM, Ronald; GAO, Xiaolei; BOGA, Sobhana Babu; YU, Younong; WU, Hao; LIU, Shilan; YANG, Chundao; (102 pag.)WO2016/164284; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of Compound 1 (5.0 g, 21.5 mmol) and ethyl 2-diazoacetate (3.2 g, 28.1 mmol) in THF (100 mL) was added BF3-Et2O (2.7 mL, 21.5 mmol) at -78 C. under N2. The reaction mixture was stirred at -78 C. for 1.5 h, then warmed to 28 C. slowly and stirred for 1.5 h. The resulting mixture was quenched with NaHCO3 (sat.) and extracted with EA (300 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude product, which was purified by flash column chromatography to give a mixture of Compound 2 and 3 (3.4 g, 50%). LCMS: 320.0 [M+1]., 61995-20-8

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hartman, George D.; US2015/197493; (2015); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

To a solution of PPh3CH3Br (230 g, 0.64 mol) in THF (0.8 L) is added a solution of n- BuLi (240 mL, 0.6 mol) at 0C under N2. The mixture is stirred at 0C for 1 h then R-7 (100 g, 0.43 mol) in THF (0.8 L) is added to the reaction mixture at 0C. The mixture is allowed to warm to ambient temperature, stirred for 1 h, then poured into H20 and extracted with EtOAc. The organic layers are washed with brine, dried with Na2S04, concentrated and purified by flash chromatography (Si02, Hep to 25%EtOAc in Hep) to give compound R-8 (45 g, 45%). To a solution of R-8 (20.0 g, 86 mmol) in 1,4-dioxane (200 mL) is added Zn-Cu (33.2 g, 259 mmol) at rt under N2. Trichloroacetyl chloride (31.4 g, 173 mmol) in 1,4-dioxane (200 mL) is added. The mixture is allowed to warm to rt and stirred for 2 days. The mixture is treated with aqueous NaHCC>3 and extracted with EtOAc. The organic layers are washed with brine, dried with Na2S04, concentrated and purified by flash chromatography (Si02, Hep to 25 EtOAc in Hep) to give R-9 (11 g, 34%).

As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BENTZIEN, Joerg; BERRY, Angela; BOSANAC, Todd; BURKE, Michael, J.; DISALVO, Darren; MAO, Can; MAO, Wang; SHEN, Yue; WO2015/116485; (2015); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

61995-20-8, To a solution of trimethylsulfoxonium iodide (3.1 g) in dimethyl sulfoxide (40 mL) was added sodium hydride (570 mg), and the mixture was stirred at room temperature for 1 hr. A solution of benzyl 3-oxopiperidine-1-carboxylate (3.0 g) in dimethyl sulfoxide (10 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 16 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give the object product (1.9 g, 60%). 1H NMR (300 MHz, CDCl3) delta ppm 1.64-1.88 (m, 4H) 2.65-2.71 (m, 2H) 3.42-3.54 (m, 4H) 5.13 (s, 2H) 7.25-7.37 (m, 5H)

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Taniguchi, Takahiko; Miyata, Kenichi; Kubo, Osamu; US2010/69351; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

61995-20-8,61995-20-8, Benzyl 3-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of trimethylsulfoxonium iodide (35.20 g, 0.16 mol) in t-BuOH (150 mL) was added t-BuOK (17.95 g, 0.16 mol) at 50C , the mixture turned to a cloudy suspension. The mixture was stirred at the same temperature for 1.5h. Compound 5-C (14.90 g, 64 mmol) was then added at that temperature and the mixture stirred at 50C for another 48h. The reaction mixture was cooled to room temperature and partitioned between saturated aqueous NH4CI and EtOAc. The organic phase was separated, dried (MgS04), filtered and concentrated under reduce pressure. The residue obtained was purified silica gel columnchromatography (EtOAc/Pet ether=1/6) to give (2.0 g, 1 1 %) as colorless oil. The structure was confirmed by LC-MS and H-NMR spectra. TLC: Rf=0.52 silica gel EtOAc/Pet ether=1/1 LC-MS : 262 ([M+1]+), H-NMR: 7.33 (m, 5H), 5.14 (s, 2H), 4.66 – 4.43 (m, 2H), 3.82 (d, J = 13.0 Hz, 1 H), 3.67 – 3.07 (m, 3H), 2.37 (m, 2H), 1.99 – 1.35 (m, 4H).

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; YM BIOSCIENCES AUSTRALIA PTY LTD; BURNS, Christopher John; WO2014/32; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

Part A. Preparation of N-(benzyloxycarbonyl)-2-phenylmethyl-3-piperidone. A stirring solution of N-(benzyloxycarbonyl)-3-piperidone (1000 mg, 4.25 mmol) and pyrrolidine (454 mg, 6.38 mmol, Aldrich) in dry toluene (10 mL) in a round bottom flask fitted with a Dean-Stark trap was refluxed for 4 h. The reaction was conc. in vacuo to a orange oil. The oil was dissolved in dry acetonitrile (10 mL) and then benzyl bromide (800 mg, 4.68 mmol, Aldrich) was added. The reaction was heated to reflux for 16 h and then cooled to room temperature. The reaction was quenched by the addition of 1M HCl (50 mL) and then extracted with EtOAc (4*40 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and conc. in vacuo to an oil. The oil was purified by flash chromatography (SiO2, 7-20% EtOAc in hexanes) to yield 86 mg of the product as a white solid. MS (ESI) 324 (M+H).

61995-20-8 Benzyl 3-oxopiperidine-1-carboxylate 1514169, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Ko, Soo S.; DeLucca, George V.; Duncia, John V.; Santella, III, Joseph B.; Wacker, Dean A.; US6331545; (2001); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

crude purified product (770 mg) of benzyl 3-oxopiperidine-1-carboxylate, 2,2-dimethylpropan-1-amine (643 mg) and acetic acid (0.5 mL) were dissolved in THF (10 mL), and sodium triacetoxyborohydride (1563 mg) was added at room temperature. The mixture was stirred at room temperature for 1 hr, to the reaction mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in THF (10 mL), di-tert-butyl dicarbonate (1610 mg) and triethylamine (2.57 mL) were added at room temperature, and the mixture was stirred at 60 C. for 6 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (690 mg) as a colorless oil. (1235) 1H NMR (300 MHz, CDCl3) delta 0.89 (9H, brs), 1.31-1.53 (10H, m), 1.66-1.95 (2H, m), 2.10-3.82 (6H, m), 3.99-4.27 (2H, m), 4.99-5.22 (2H, m), 7.28-7.41 (5H, m)., 61995-20-8

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; AIDA, Jumpei; YOSHITOMI, Yayoi; HITOMI, Yuko; NOGUCHI, Naoyoshi; HIRATA, Yasuhiro; FURUKAWA, Hideki; SHIBUYA, Akito; WATANABE, Koji; MIYAMOTO, Yasufumi; OKAWA, Tomohiro; TAKAKURA, Nobuyuki; MIWATASHI, Seiji; (199 pag.)US2016/115128; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

To a solution of Compound 1 (5.0 g, 21.5 mmol) and ethyl 2-diazoacetate (3.2 g, 28.1 mmol) in THF (100 mL) was added BF3-Et2O (2.7 mL, 21.5 mmol) at -78 C. under N2. The reaction mixture was stirred at -78 C. for 1.5 h, then warmed to 28 C. slowly and stirred for 1.5 h. The resulting mixture was quenched with NaHCO3 (sat.) and extracted with EA (300 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude product, which was purified by flash column chromatography to give a mixture of Compound 2 and 3 (3.4 g, 50%). LCMS: 320.0 [M+1]. To a suspension of NaH (338 mg, 8.5 mmol) in THF (30 mL) was added a solution of a mixture of Compound 3 and Compound 3?(2.7 g, 8.5 mmol) in THF (30 mL) at 0 C. under N2, and stirred at rt for 0.5 h. A solution of Select F (2.7 g, 8.5 mmol) in DMF (15 mL) was added dropwise. The reaction mixture was stirred at r.t. for 3 h. The resulting mixture was quenched with NH4Cl and extracted with EA (200 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by flash column chromatography to give Compound 4 (1.0 g, 35%) and Compound 4? (0.9 g, 32%). Compound 4: 1H NMR (400 MHz, CDCl3) delta=7.28-7.39 (m, 5H), 5.18 (s, 2H), 4.40-4.68 (m, 1H), 4.11-4.39 (m, 3H), 3.45-3.63 (m, 1H), 3.21-3.38 (m, 1H), 1.85-2.45 (m, 4H), 1.26-1.30 (m, 3H). Compound 4?: 1H NMR (400 MHz, CDCl3) delta=7.28-7.40 (m, 5H), 5.14-5.18 (m, 2H), 4.24-4.47 (m, 4H), 3.88-4.00 (m, 1H), 3.09-3.25 (m, 1H), 2.85-2.91 (m, 2H), 1.92-1.95 (m, 2H), 1.27-1.35 (m, 3H).

61995-20-8 Benzyl 3-oxopiperidine-1-carboxylate 1514169, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Hartman, George D.; US2015/197493; (2015); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

Intermediate 11Phenylmethyl 3-{[2-({[(1 ,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-1 – piperidinecarboxylate (D11) Phenylmethyl 3-oxo-i-piperidinecarboxylate (5 g, 21.44 mmol) was dissolved in a mixture of methanol (200 ml) and acetic acid (1.227 ml, 21.44 mmol). 1 ,1- dimethylethyl (2-aminoethyl)carbamate (10.30 g, 64.3 mmol) was added and sodium triacetoxyborohydride (11.36 g, 53.6 mmol) was also added after stirring for 1 hour. The reaction mixture was allowed to stir for a further 4 hours. Sodium bicarbonate (9.00 g, 107 mmol) was added to the reaction and the resulting mixture was concentrated in vacuo. The resulting residue was redissolved using DCM and water. The mixture was basified to pH 14 using 2M NaOH and the aqueous layer was extracted with DCM. The combined organic extracts was passed through a hydrophobic frit and concentrated in vacuo. The resulting residue was purified by silica column chromatography (Biotage SP4, eluting with a gradient from 0-20% MeOH in DCM) to give the title compound as a yellow oil (7.85 g, 20.80 mmol, 97 % yield).MS ES+ve m/z 275 (M+H)1H NMR (400 MHz, DMSO-D6) delta ppm 1.2 (m, 1 H) 1.4 (m, 1 H) 1.4 (s, 9 H) 1.6 (m, 2 H) 1.8 (m, 1 H) 2.4 (m, 1 H) 2.6 (m, 2 H) 2.7 (m, 1 H) 2.9 (m, 3 H) 3.7 (m, 1 H) 3.8 (m, 1 H) 5.1 (s, 2 H) 6.7 (m, 1 H) 7.3 (m, 5 H)

As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; BESWICK, Paul, John; GLEAVE, Robert, James; WO2010/91721; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

General procedure: The reaction mixture containing 200 mM substrate, 1mM NAD+, 5% (v/v) 2-propanol and 10mg crude enzyme READH in 1mL potassium phosphate buffer (100mM, pH 7.0) was incubated at 50 C. For ChKRED20, 40% (v/v) 2-propanol and a reaction temperature of 40 C were applied instead. The reaction was monitored by TLC, and terminated by extracting with methyl tert-butyl ether (1 mL). The organic extract was dried over anhydrous sodium sulfate and concentrated. The samples were subjected to chiral HPLC to determine the conversion and enantiomeric excess. The products were purified by silica gel column chromatography, and identified by NMR analysis, optical rotation measurements and mass spectrometry.

As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role.

Reference：
Article; Li, Chao; Liu, Yan; Pei, Xiao-Qiong; Wu, Zhong-Liu; Process Biochemistry; vol. 56; (2017); p. 90 – 97;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem