1-叔丁氧羰基-2,5-二氢-1H-吡咯-3-硼酸频哪醇酯

1-叔丁氧羰基-2,5-二氢-1H-吡咯-3-硼酸频哪醇酯 - Names and Identifiers

Name	1-Boc-2,5-Dihydro-1H-pyrrole-3-boronicacidpinacolester
Synonyms	1-Boc-2,5-Dihydro-1H-pyrrole-3-boronicacidpinacolester 1-boc-2,5-dihydro-1h-pyrrole-3-boronic acid pinacol ester tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl 1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid pinacol ester tert-butyl 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxyl TERT-BUTYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2,5-dihydro-1h-pyrrole-1-carboxylate 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylic acid, tert-butyl ester 2,5-Dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylic Acid 1,1-DiMethylethyl Ester 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethyl ester
CAS	212127-83-8

1-叔丁氧羰基-2,5-二氢-1H-吡咯-3-硼酸频哪醇酯 - 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

1-叔丁氧羰基-2,5-二氢-1H-吡咯-3-硼酸频哪醇酯 - 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