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Product Name:1-Boc-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine
CAS:286961-14-6
Purity:98% Min. Package:100g;1kg;5kg,10kg,25kg,50kg
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| | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Basic information |
| Product Name: | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester | | Synonyms: | N-BOC-1,2,5,6-TETRAHYDROPYRIDINE-4-(PINACOLATO)BORONATE;(N-TERT-BUTOXYCARBONYL)-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER;4-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-N-BOC-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE;1-N-BOC-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE 98+%;N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester;1-Boc-4-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine;tert-butyl 4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-
1,2,3,6-tetrahydropyridine-1-carboxylate | | CAS: | 286961-14-6 | | MF: | C16H28BNO4 | | MW: | 309.21 | | EINECS: | 689-148-0 | | Product Categories: | API intermediates;Organoborons;Pyridine | | Mol File: | 286961-14-6.mol |  |
| | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Chemical Properties |
| Melting point | 114.0 to 118.0 °C | | Boiling point | 348.0±52.0 °C(Predicted) | | density | 1.05±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform (Sparingly), Dichloromethane (Sparingly), DMSO (Slightly) | | form | Solid | | pka | -1.21±0.40(Predicted) | | color | white to off-white | | Water Solubility | Soluble in most organic solvents. Insoluble in water. | | InChI | InChI=1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3 | | InChIKey | VVDCRJGWILREQH-UHFFFAOYSA-N | | SMILES | C1N(C(OC(C)(C)C)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37-60 | | WGK Germany | 3 | | TSCA | No | | HazardClass | IRRITANT | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Usage And Synthesis |
| Chemical Properties | off-white powder | | Uses | Reagent used for suzuki-Miyaura cross-coupling using palladium phosphine catalyst, palladium-catalyzed ligand-controlled regioselective Suzuki coupling, wrenchnolol derivative optimized for gene activation in cells. Also used in Preparation of several enzymatic inhibitors and receptor ligands, orally active anaplastic lymphoma kinase inhibitors and oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes. | | Uses | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester is an intermediate for organic synthesis and pharmaceutical research and development, and can be used for suzuki reaction. | | Synthesis | The general procedure for the synthesis of 1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine from tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate and bipinacolato pinacol ester was carried out as follows: to a dry reaction flask, bis(pinacolato)diboron ( 3.37 g, 13.28 mmol), potassium acetate (KOAc, 3.58 g, 36.46 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PDCL2DPPF, 0.27 g, 0.36 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.2 g, 0.36 mmol) to a dry reaction flask, and the reaction system was subsequently flushed with argon to flush the reaction system. A solution of tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (4.00 g, 12.07 mmol) in dioxane (35 mL) was added, and the reaction mixture was stirred at 80 °C overnight. After completion of the reaction, it was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (EtOAc, 50 mL). The organic layer was separated, washed with saturated saline (50 mL), dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product was purified by fast column chromatography (eluent ratio of 9:1 hexane:ethyl acetate) to give the target product as a white solid (4.5 g, 100% yield). | | References | [1] Patent: WO2004/58727, 2004, A1. Location in patent: Page 53-54
[2] Patent: WO2014/100501, 2014, A1. Location in patent: Paragraph 00727; 00728
[3] Patent: WO2015/200534, A2. Location in patent: Paragraph 00297; 00586; 00643
[3] Patent: , 2015, . Location in patent: Paragraph 00297; 00586; 00643
[5] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 59-60 |
| | N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Preparation Products And Raw materials |
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