Hydrochloric Acid → 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

HRID 1926320Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([B:19]3[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:28]>O1CCOCC1>[ClH:28].[CH3:26][C:21]1([CH3:27])[C:22]([CH3:24])([CH3:25])[O:23][B:19]([C:17]2[CH:16]=[N:15][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:18]=2)[O:20]1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.011 g, 2.68 mmol, 1 eq.) in dioxane (5 mL), 4.0 M of HCl in dioxane (10 mL, 20 eq) was added and the reaction was stirred at 35° C. for 2.5 h. The reaction mixture was concentrated in vacuo, yielding the title material, as a white solid. 1H NMR (400 MHz, CDCl3): δ=1.32 (s, 12H), 2.46 (br s, 4H), 3.18 (br s, 2H), 3.57-3.70 (m, 2H), 4.48 (br s, 1H), 7.78 (s, 1H), 7.79 (s, 1H), 9.54-10.04 (m, 2H). MS (ES+): m/z=278.14 (100) [MH+]. HPLC: tR=1.89 min (ZQ2, polar—5 min).

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-17222ba6054d4d6984568d6045ad0f88
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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