| Identification | More | [Name]
4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE | [CAS]
568577-88-8 | [Synonyms]
4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]MORPHOLINE
4-(MORPHOLINO)PHENYLBORONIC ACID PINACOLATE
4-MORPHOLINOPHENYLBORONIC ACID, PINACOL ESTER
4-Morpholin-4-ylbenzeneboronic acid pinacol ester
4-[4-(4,4,5,5-Tetramethyl-1,2,3-dioxaborolan-2-yl)phenyl]morpholine | [Molecular Formula]
C16 H24 B N O3 | [MDL Number]
MFCD04112544 | [Molecular Weight]
289.18 | [MOL File]
568577-88-8.mol |
| Hazard Information | Back Directory | [Uses]
4-(4-Morpholinyl)benzeneboronic acid pinacol ester is used as pharmaceutical intermediate. | [Synthesis]
General procedure for the synthesis of 4-(4-morpholinyl)phenylboronic acid pinacol ester from 4-(4-bromophenyl)morpholine and pinacolborane: To a solution of 4-(4-bromophenyl)morpholine (20 g, 82.64 mmol) in dioxane (200 ml) were added pinacolborane (13.2 g, 99.17 mmol), dichlorobis(triphenylphosphine)palladium(II) (3 g 4.13 mmol) and triethylamine (34.5 ml, 247.93 mmol). The reaction mixture was heated under reflux conditions for 4 hours. After completion of the reaction, the mixture was poured into water. After extraction with dichloromethane, the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane) to afford 4-(4-morpholinyl)benzeneboronic acid pinacol ester as an orange oil, which crystallized after cooling (19.98 g, 83.94% yield); APCI-MS m/z 289.07 ([M+H]+). | [References]
[1] Patent: WO2004/13135, 2004, A1. Location in patent: Page 48-49
[2] Patent: WO2004/16606, 2004, A1. Location in patent: Page 25
[3] Patent: WO2004/13138, 2004, A2. Location in patent: Page 23; 24 |
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