| Identification | Back Directory | [Name]
TERT-BUTYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE | [CAS]
212127-83-8 | [Synonyms]
(containing ca. 50% 4,5-dihydro isomer)
1-Boc-2,5-dihydropyrrole-3-boronic Acid Pinacol Ester
N-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
(1-(TERT-BUTOXYCARBONYL)-2,5-DIHYDRO-1H-PYRROL-3-YL)BORONIC ACID PINACOL ESTER
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE
tert-butyl 3-(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-pyrrole-1-carboxylate
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-carboxylat
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 | [Molecular Formula]
C15H26BNO4 | [MDL Number]
MFCD10697918 | [MOL File]
212127-83-8.mol | [Molecular Weight]
295.18 |
| Chemical Properties | Back Directory | [Boiling point ]
330.5±52.0 °C(Predicted) | [density ]
1.06±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
solid | [pka]
-1.18±0.40(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C15H26BNO4/c1-13(2,3)19-12(18)17-9-8-11(10-17)16-20-14(4,5)15(6,7)21-16/h8H,9-10H2,1-7H3 | [InChIKey]
OIZXJJIHVIYNKZ-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1 |
| Hazard Information | Back Directory | [Uses]
2,5-Dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylic Acid 1,1-Dimethylethyl Ester, in the synthesis of series of kinase inhibitors.
| [Synthesis]
General procedure for the synthesis of tert-butyl 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol ester from tert-butyl 3-(trifluoromethanesulfonyloxy)-2H-pyrrole-1(5H)-carboxylate and pinacol ester of bis(boronic acid): tert-butyl 3-(trifluoromethanesulfonyloxy)-2,5-dihydro-pyrrole-1-carboxylate (2.00 g, 6.3 mmol) was dissolved in 1,4 -dioxane (35 mL) and degassed potassium acetate (1.86 g, 18.9 mmol), Pd(dppf)Cl2-CH2Cl2 (154 mg, 0.19 mmol), dppf (105 mg, 0.19 mmol), and bis(pinacolato)ethylborane (1.92 g, 7.56 mmol) were added sequentially to this solution under nitrogen protection . The reaction mixture was stirred and reacted at 80 °C overnight. Upon completion of the reaction, the crude reaction mixture was concentrated and purified by fast column chromatography on silica gel (15-50% EtOAc/hexane gradient elution) to afford tert-butyl 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydro-pyrrole-1-carboxylate as a white semi-solid (1.50 g, 81% yield).1H NMR (CDCl3, 300 MHz) δ 1.26 (s, 12H), 1.46 (s, 9H), 4.18 (m, 4H), 6.45 (bd, 1H, J = 14.10 Hz); MS (ESI) m/z = 240.2 (MH+ -t-Bu). | [References]
[1] Patent: US2010/204265, 2010, A1. Location in patent: Page/Page column 91; 92
[2] Patent: TW2016/4185, 2016, A. Location in patent: Paragraph 0142; 0143
[3] Patent: WO2010/5783, 2010, A1. Location in patent: Page/Page column 152
[4] Patent: WO2016/65236, 2016, A1. Location in patent: Page/Page column 125
[5] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 58-59 |
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