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ChemicalBook CAS DataBase List tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]piperidine-1-carboxylate
889865-34-3

tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]piperidine-1-carboxylate synthesis

5synthesis methods
109384-19-2 Synthesis
N-BOC-4-Hydroxypiperidine

109384-19-2
393 suppliers
$5.00/1g

269409-70-3 Synthesis
4-Hydroxyphenylboronic acid pinacol ester

269409-70-3
250 suppliers
$11.00/1g

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Yield:889865-34-3 264 mg

Reaction Conditions:

with di-isopropyl azodicarboxylate;triphenylphosphine in tetrahydrofuran at 20;Inert atmosphere;Temperature;

Steps:

2.1 Step 1: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenoxy)piperidine-1-carboxylate

To a 100 ml round bottom flask were added under an argon atmosphere 4- hydroxyphenylboronic acid pinacol ester (257 mg, 1.168 mmol), tert-butyl 4- hydroxypiperidine-1-carboxylate (264 mg, 1.285 mmol), PPh3 (337 mg, 1.285 mmol) and THF (5 ml). DIAD (0.250 ml, 1.285 mmol) was added dropwise and the RM was stirred at RT overnight. The RM was pourred into a mixture of EtOAc and an aq. sat. solution of Na2CO3, the aq. phase was extracted with EtOAc, the combined organic phases were washed with brine, dried over MgSO4 and the residue was purified by chromatography on silica gel eluting with EtOAc (from 0 % to 20 %) in CHX, yielding the title compound as a solid (264 mg). Method D: Rt = 1.49 min; [M-tBu+H]+= 348.

References:

WO2021/55295,2021,A1 Location in patent:Page/Page column 302; 303; 443; 444