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

HRID 389453Notes

Reaction equation

[CH3:1][C:2]1([CH3:27])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:13]=2)[O:3]1.[ClH:28]>O1CCOCC1>[ClH:28].[CH3:1][C:2]1([CH3:27])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)[O:3]1

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (5.02 g, 13.3 mmol) in 1,4-dioxane (40 mL) was treated with HCl (4.0 M in 1,4-dioxane, 50 mL, 200 mmol) and stirred at 35° C. for 3 h. The reaction mixture was concentrated in vacuo to a white solid, affording 5.01 g (100%) of the title compound. The material was used without additional purification. 1H NMR (400 MHz, CDCl3) δ 1.33 (s, 12H), 2.50 (br s, 4H), 3.09-3.41 (m, 2H), 3.57-3.79 (m, 2H), 4.73 (br s, 1H), 7.87 (s, 2H), 9.82 (br s, 2H); MS (ESI): 278.15 [M+H]+; HPLC tR=2.01 min.

Workup

concentrationThe reaction mixture was concentrated in vacuo to a white solid

Sources & evidence

ORD record: ord-8e77bb74925f40c19414166ae4c3b3e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

Loading…