Methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester synthesis

7synthesis methods

Product Name:Methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester
CAS Number:916587-44-5
Molecular formula:C18H28BNO4
Molecular Weight:333.23

330793-01-6 Synthesis

4-(N-Boc-amino)phenylboronic acid pinacol ester

330793-01-6
172 suppliers
$7.00/250mg

74-88-4
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$15.00/10g

Methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester

916587-44-5
31 suppliers
$40.00/250mg

Yield:916587-44-5 70%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide;mineral oil at 20; for 18 h;

Steps:

2.1 Example 2 N-hydroxy-N'-methyl-2-(methyl{[4'-(methylamino)biphenyl-4-yl]carbonyl}amino)propanediamide (Compound 2)

(1) 60% Sodium hydride (0.55 g) and methyl iodide (1.2 mL) were added to a DMF (6.0 mL) solution of t-butyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (2.0 g), and the mixture was stirred for 18 hours at room temperature. Ethyl acetate and water were added to the reaction mixture, and the organic layer was isolated. The extract was washed sequentially with water and brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, whereafter the solvent was distilled off under reduced pressure. Hexane was added to the residue, and the precipitated solid was collected by filtration to obtain t-butyl=methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (white solid) (1.46 g, 70%).¹ H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34 (12H, s), 1.45 (9H, s), 3.27 (3H, s), 7.24 (2H, d, J=8.4 Hz), 7.76 (2H, d, J=8.4 Hz)

References:

EP2562155,2013,A1 Location in patent:Paragraph 0222-0223