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

HRID 2046916Notes

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 (3.02 g, 8.00 mmol) in 1,4-dioxane (30 mL, 400 mmol), 4.0 M of HCl in 1,4-Dioxane (30 mL) was added and the reaction was stirred at 35° C. for 3 h. The reaction mixture was concentrated in vacuo to a white solid. The material was slightly hygroscopic. All free-flowing material was transferred to a vial and dried under vacuum for several hours. The material thus obtained was used in further reactions without purification. 1H NMR (400 MHz, CDCl3): δ=1.33 (s, 12H), 2.49 (br s, 4H), 3.18 (br s, 2H), 3.59-3.70 (m, 2H), 4.71 (br s, 1H), 7.87 (s, 2H), 9.84 (br s, 2H). MS (ES+): m/z 278.11 (100) [MH+]. HPLC: tR=1.99 min (ZQ3, polar—5 min).

Workup

concentrationThe reaction mixture was concentrated in vacuo to a white solid
customdried under vacuum for several hours
customThe material thus obtained
customwas used in further reactions without purification
custom5 min

Sources & evidence

ORD record: ord-e606529e23dd4fc589059146cf0decf3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592448B2

Reaction notes

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