ChemicalBook CAS DataBase List 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine

1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine synthesis

5synthesis methods

Product Name:1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine
CAS Number:912369-50-7
Molecular formula:C16H25BN2O2
Molecular Weight:288.19

470478-90-1 Synthesis

4-(4-TERT-BUTOXYCARBONYLPIPERAZINYL)PHENYLBORONIC ACID, PINACOL ESTER

470478-90-1
166 suppliers
$9.00/250mg

1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine

912369-50-7
62 suppliers
$120.00/0.25g

Yield:912369-50-7 72%

Reaction Conditions:

with trimethylsilyl trifluoromethanesulfonate in dichloromethane at 0 - 20; for 3 h;Inert atmosphere;

Steps:

D Step D:
Step D:
1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine
Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (1.6 g, 4.12 mmol, 1.00 equiv) in dichloromethane (40 mL), followed by the addition of TMSOTf (1.5 g, 6.75 mmol, 1.60 equiv) dropwise with stirring at 0° C.
To the above solution was added 6-dimethylpyridine (132.5 mg, 1.00 mmol, 0.30 equiv).
The resulting solution was stirred for 3 hours at room temperature.
The reaction was then quenched by the addition of 50 mL of saturated sodium bicarbonate aqueous.
The resulting solution was extracted with ethyl acetate (30 mL*3).
The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10:1).
This resulted in 854.0 mg (72%) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine as off-white solid. LCMS (ES⁺): m/z 289.15 [M+H]⁺.

References:

Arvinas, Inc.;Yale University;Crew, Andrew P.;Hornberger, Keith R.;Wang, Jing;Dong, Hanqing;Qian, Yimin;Crews, Craig M.;Jaime-Figueroa, Saul US2018/179183, 2018, A1 Location in patent:Paragraph 1400

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