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Hydrogen chloride-ethyl acetate → 4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine hydrochloride

HRID 57578
Notes
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Reaction equation

HRID 57578 reaction equation
[CH3:1][C:2]1([CH3:28])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1.[ClH:29].CC(=O)OCC>CC(=O)OCC>[ClH:29].[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:28])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 53629760tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 867173724-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate (3.0 g, 7.75 mmol) and 10 mL of HCl-EA (5.0 N) in 20 mL of EA was stirred at room temperature for 2 hours. The volatiles were removed in vacuo to give 2.6 g of title compound. MS (m/z)=288 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-b39ec787ed144b598f5f65998fc9ea0f
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes