tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate Chemical Properties

Boiling point:

480.6±45.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-1.69±0.40(Predicted)

Appearance

White to off-white Solid

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-(1-Boc-4-piperidinyl)phenylboronic acid pinacol ester from 1-N-Boc-4-(4-bromophenyl)piperidine and pinacol ester of boronic acid was as follows: in a pressure tube, a dioxane solution of tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate (1363 mg, 4.006 mmol) was purified with bis(pinacolato)diboron (1526 mg , 6.009 mmol), KOAc (1179 mg, 12.02 mmol) and PdCl2(dppf)-DCM (327.1 mg, 0.4006 mmol) treatment. The mixture was bubbled with nitrogen for 1 min, then sealed and heated at 100 °C overnight. After the reaction mixture was cooled to ambient temperature, it was diluted with a mixture of EtOAc (75 mL), water (50 mL), and brine (25 mL), and the resulting emulsion was filtered through Celite and washed with EtOAc. The two-phase filtrate was separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuum. Purification of the crude product by silica gel chromatography (0-50% EtOAc/hexane) afforded 4-(1-Boc-4-piperidinyl)phenylboronic acid pinacol ester (1437 mg, 93% yield).1H NMR (CDCl3) δ 7.76 (d, 2H), 7.22 (m, 2H), 4.24 (d, 2H), 2.79 (dt, 2H), 2.65 ( tt, 1H), 1.81 (m, 2H), 1.63 (dq, 2H), 1.48 (s, 9H), 1.33 (s, 12H).

References

[1] Patent: WO2017/11776, 2017, A1. Location in patent: Paragraph 00701
[2] Patent: WO2017/114497, 2017, A1. Location in patent: Page/Page column 339
[3] Patent: WO2018/59549, 2018, A1. Location in patent: Page/Page column 293
[4] Patent: WO2007/126957, 2007, A2. Location in patent: Page/Page column 101
[5] Patent: WO2009/7390, 2009, A2. Location in patent: Page/Page column 96

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate(956136-85-9)Related Product Information

• TERT-BUTYL 4-(4-BROMOPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE
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• tert-Butyl 4-aMino-4-(4-broMophenyl)piperidine-1-carboxylate
• 4-(3-BROMO-PHENYL)-1-N-BOC-PIPERIDINE
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