1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethyl ester
1-Boc-2,5-Dihydro-1H-pyrrole-3-boronicacidpinacolester
CAS: 212127-83-8
Molecular Formula: C15H26BNO4
1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethyl ester - Names and Identifiers
1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethyl ester - Physico-chemical Properties
| Molecular Formula | C15H26BNO4 |
| Molar Mass | 295.18 |
| Density | 1.06±0.1 g/cm3(Predicted) |
| Boling Point | 330.5±52.0 °C(Predicted) |
| pKa | -1.18±0.40(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethyl ester - Reference Information
| Application | 1-tert-butoxycarbonyl-2, 5-dihydro-1H-pyrrole-3-borate pinacol ester is a borate ester compound. In scientific research, borate compounds are mainly used as a kind of synthetic intermediates in transition metal-catalyzed cross-coupling reactions to construct target compounds with more complex structures. In industrial production, borate compounds have been widely used in the fields of medicine, pesticides and materials. |
| preparation | adding tert-butyl 3-oxopyrrolidin-1-formate (20.0g,0.11mol,1.0 equivalent) and THF(200mL) to the flask dried under N2. The solution was cooled in an acetone ice bath (-78°C). LiHMDs(125mL,0.12mol,1.15 equivalents) (1M solution in THF) were added to it. The reaction mixture was stirred at -78°C for 30min, and then a solution of 1,1, 1-trifluoro-N-phenyl-N-((trifluoromethyl) sulfonyl) methane sulfonamide (46.3g,0.13mol,1.2 equivalent) in THF(200mL) was added dropwise. The reaction mixture was stirred for 30min, then the temperature was raised to 0 ℃ and stirred for 1.5h. The reaction mixture was quenched with a saturated sodium bicarbonate solution and then extracted with ethyl acetate. The combined extract was washed with brine, dried with sodium sulfate, filtered, and evaporated. The crude product was purified by column chromatography (PE/EA = 30/1,v/v) to give 3-(((trifluoromethyl) sulfonyl) oxy)-2, 5-dihydro-1H-pyrrole-1-formate tert-butyl ester (20.5g,59.8%). 3-trifluoromethane sulfonyl -2, 5-dihydro-pyrrole-1-formate tert-butyl ester (21.0g,66.2mmol,1.0 equivalent) was dissolved in 1, 4-dioxane (300mL), and the above solution was added to potassium acetate (19.5g,200.0mmol,3.0 equivalent), Pd(dppf)Cl2 · CH2Cl2(2.7g,3.3mmol) under N2, 0.05 equivalent), DPPF(1.84g,3.3mmol,0.05 equivalent), bis (pinacol) diborane (20.0g,79.5mmol,1.2 equivalent) degassing mixture, and the reaction mixture is heated overnight at 90°C. The crude reaction mixture was concentrated and purified by rapid column chromatography (PE/EA = 10/1,v/v) to obtain 1-tert-butoxycarbonyl-2, 5-dihydro-1H-pyrrole-3-borate pinacol ester (11.4g,58.3%). |
Last Update：2024-04-10 22:29:15
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CAS: 212127-83-8
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