Category: 122860-33-7

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step C Preparation of benzyl 4-[(2-ethoxy-2-oxoethoxy)methyl]-1-piperidine carboxylate Dissolved the alcohol (3.5 g, 13.35 mmol) from Step B in CH2Cl2 (25 ml), then added rhodium diacetate dimer (30 mg, 0.067 mg) to the solution, followed by the dropwise addition of ethyl diazoacetate (1.5 ml, 14.7 mmol). N2 gas evolved as the reaction proceeded. Filtered the reaction through celite and removed solvent on the rotary evaporator, then purified by flash chromatography to yield the pure title compound (3.5 g, 78%).

122860-33-7, The synthetic route of 122860-33-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Scarborough, Robert M.; Mehrotra, Mukund; Pandey, Anjali; Smyth, Mark; US2003/55244; (2003); 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.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To oxalyl chloride (10.3 mL, 0.120 mol) in 150 mL of DCM and at -78 C, a solution of DMSO (17.1 mL, 0.241 mol) in DCM (25 mL) was added dropwisely. After 30 min, benzyl 4- (hydroxymethyl)-piperidine-l-carboxylate (20 g, 0.080 mol) in DCM (25 mL) was added dropwisely. After 30 min, Et3N (44.7 mL, 0.321 mol) was added. The resulting solution was stirred for 30 min at -78 C. The reaction was diluted with water, extracted with DCM (3 x). Combined organic layers were washed with water (3 x 500 mL), dried over Na2S04, filtered and concentrated to give Intermediate 6C (18.5 g, 93.0%). MS (ESI) m/z 247 (M+H)+.

122860-33-7, The synthetic route of 122860-33-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; THIBEAULT, Carl; CLARK, Charles, G.; DELUCCA, Indawati; HU, Carol, Hui; JEON, Yoon; LAM, Patrick, Y., S.; QIAO, Jennifer, X.; YANG, Wu; WANG, Yufeng; WANG, Tammy, C.; WO2014/22349; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 25;. N-Benzyloxycarbonyl-4- (formyl)-piperidine (E-13).; A stirred suspension of N-(benzyloxycarbonyl)-4-hydroxymethyl)-piperidine (E-12,2 g, 8 mmol) and CeliteTM (4 g) in dry DCM (120 mL) at room temperature was treated with pyridinium chlorochromate (3.5 g, 16.0 mmol), stirred for 3 hours, and filtered on Celte. The filtrate was evaporated to a dark residue which was purified by column chromatography using a gradient of 25 to 50 % EtOAc in hexane as eluant to give 1.5 g (75 %) of aldehyde E-13 as a clear oil which was immediately used in the next step : 1H NMR (CDC13) 8 1.43 (dd, 2H, J=10), 1.78 (m, 2H), 2.31 (m, 1H), 2.91 (t, 2H, J=10. 6), 3.96 (m, 2H), 5.05 (s, 2H), 7.24 (m, 5H), 9.52 (s, 1H).

122860-33-7, 122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BIOAXONE THERAPEUTIQUE INC.; WO2005/80394; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Triphenylphosphine (7.87 g, 30 mmol) and imidazole (2.05 g, 30 mmol, 1.5 equiv) in DCM at 0 0C under Ar was treated with I2 (7.61 g, 30 mmol, 1.5 equiv). After 5 min, benzyl 4-(hydroxymethyl)tetrahydro-l(2H)-pyridinecarboxylate (5.00 g, 20 mmol) in DCM was added. The reaction was stirred for 1 h and then quenched with 10% HCl. The reaction mixture was extracted with EtOAc and the organic layer was washed with NuaHCO3(sat). The organics were dried with NaCl(sat) and Na2SO4(s) and then removed under reduced pressure. The residue was then purified by column chromatography utilizing an ISCO system (EtOAc- hexane) to give 6.20 g (86%) of a white solid; m/z 360., 122860-33-7

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference：
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/24834; (2006); 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.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Reference Example 2 N-CBZ-4-iodomethylpiperidine This compound is prepared according to the procedure disclosed in U.S. Pat. No. 5,538,984. Triphenylphosphine (31.2 gr) was added to a mixture of iodine (29.4 g) in toluene (1L). After 5 min, pyridine (18 ml) was added, followed by CBZ-piperidinemethanol (34.6 gr). The resulting mixture was heated and stirred at reflux for 1.5 h. The reaction mixture was allowed to cool to room temperature, and filtered. The filtrate was washed with saturated sodium metabisulfite and brine. The organic layer was dried over MgSO4 and evaporated. The crude product was dissolved in ethyl acetate/hexane 1:5, and filtered through silica gel. The filtrate was evaporated under reduced pressure, and the crude product was crystallized from ethyl acetate/hexane., 122860-33-7

The synthetic route of 122860-33-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CHEMAGIS LTD; US2004/48893; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reaction step 2: Synthesis of benzyl 4-formylpiperidine-1-carboxylate To a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (10.0 g, 40.2 mmol, 1.0 eq) in dichloromethane (150 ml), Dess-Martin periodinane (20.4 g, 48.2 mmol, 1.2 eq) was added at at 0 C. and stirring was continued at room temperature for 12 h. After completion of the reaction (monitored by TLC, 30% ethyl acetate-hexane, Rf=0.45), the mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution, followed by brine. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with a 30-40% gradient of ethyl acetate in hexanes to obtain benzyl 4-formylpiperidine-1-carboxylate (6.2 g, 62.5%). LCMS Purity: 78.54% (ES+): m/z 248.27 (M+H+); tr=3.01 min.

122860-33-7, The synthetic route of 122860-33-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; INNOV17 LLC; Gaweco, Anderson; Tilley, Jefferson; Blinn, James; US2015/252022; (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.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 2:Oxalyl chloride (9.4 g; 74 mmol) is dissolved in DCM (55 ml) and cooled to -78C. DMSO (7.5ml; 106 mmol) is added dropwise and the mixture is stirred for 15 min at -78C. In a separateflask, 4a3 (13 g; 53 mmol) is dissolved in DCM (55 ml) and added dropwise to the first flask viacannula. Once the addition is finished, the mixture is stirred at -55C for 15 min. The reactionmixture is cooled to -78C and a solution of triethylamine (22 ml; 158 mmol) in DCM (28 ml) isadded dropwise to the reation mixture via cannula. The mixture is stirred for 1 hat -78C then15 min at ooc and 30 min at RT. The reaction is neutralized with 11 ml of AcOH and dilutedwith 100 ml of DCM and 100 ml of water. The layers are separated and the aqueous layer isextracted with DCM (2 x 100 ml). The combined organic layers are washed with brine, driedover MgS04, filtered and concentrated. Purification by Combiflash (120 g column, 0-50%EtOAc/Hex) gives 4a4., 122860-33-7

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; THIBEAULT, Carl; RANCOURT, Jean; BEAULIEU, Pierre L.; DECOR, Anne; GRAND-MAITRE, Chantal; KUHN, Cyrille; VILLEMURE, Elisia; LEBLANC, Melissa; LACOSTE, Jean-Eric; MOREAU, Benoit; JOLICOEUR, Eric; SURPRENANT, Simon; HUCKE, Oliver; WO2014/70976; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

26c. Phenylmethyl 4-formylpiperidinecarboxylate To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes. The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78 C. over a period of 15 minutes. The resultant solution was stirred at -78 C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes. The mixture was further stirred at -78 C. for 30 min and then at 0 C. for 15 min. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic phase was washed with 1% HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) delta9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H). 13C NMR (75 MHz, CDCl3) delta202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+)., 122860-33-7

122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Fang, Xinqin; Garvey, David S.; Gaston, Ricky D.; Lin, Chia-En; Ranatunga, Ramani R.; Richardson, Stewart K.; Wang, Tiansheng; Wang, Weiheng; Wey, Shiow-Jyi; US2003/203915; (2003); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

122860-33-7, Example 3; 4-Formyl-piperidine-1-carboxylic acid benzyl ester (3); Oxalyl chloride (59.1 ml_, 674 mmol) was dissolved in dichloromethane (500 ml_) and cooled to -78C. Dimethylsulfoxide (68.3 ml_, 963 mmol) was added and the mixture was stirred for 15 min. 4-Hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (2) (120 g, 481 mmol) dissolved in dichloromethane (500 ml_) was added. The mixture was allowed to warm to -55C for 15 min. The mixture was again cooled to -78C and triethylamine (205 ml_, 1443 mmol) in dichloromethane (250 ml_) was added. The suspension was allowed to warm to room temperature and quenched with glacial acetic acid (100 ml_). The solution was washed with water and the aqueous phase extracted with dichloromethane (2 x 200 ml_). The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to give 4- formyl-piperidine-1-carboxylic acid benzyl ester (119 g, 100%).

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference：
Patent; NEUROSEARCH A/S; WO2007/93603; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: benzyl 4-(iodomethyl)piperidine-1-carboxylate (1165) A solution of I2 (9.77 g, 38.50 mmol) in THF (5 mL) was added in dropwise to a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (8.00 g, 32.10 mmol), 1H-imidazole (2.62 g, 38.50 mmol) and triphenylphosphine (10.10 g, 38.50 mmol) in THF (15 mL) at ambient temperature in a period of 4 hr. The reaction mixture was then quenched with water (30 mL), diluted with water (40 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel, eluted with EtOAc/PE (1/10) to afford the title compound: LCMS (ESI) calc’d for C14H18INO2 [M+H]+: 360. found 360.

122860-33-7, 122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem