Potassium Carbonate → (4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid

HRID 1262186

Reaktionsgleichung

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[B:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)=[CH:4][CH:5]=1)([OH:11])[OH:10]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A suspension of (4-bromomethylphenyl)boronic acid (2.00 g, 9.31 mmol), thiomorpholine 1,1-dioxide (1.50 g, 11.1 mmol), and potassium carbonate (2.60 g, 18.8 mmol) in acetone (25 mL) was stirred at 40° C. for 18 hours. The mixture was cooled to room temperature and the volatiles were evaporated. The residue was suspended in saturated aqueous ammonium chloride (100 mL). The aqueous phase was decanted from the waxy solid, rinsed with water (50 mL), and decanted again. The waxy solid was dissolved in methanol (50 mL), filtered to remove insoluble salts and evaporated to obtain 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide as a tan foam (2.48 g). The recovered material was crude by 1HNMR but was used without further purification.

Aufarbeitung

temperatureThe mixture was cooled to room temperature
customthe volatiles were evaporated
customThe aqueous phase was decanted from the waxy solid
washrinsed with water (50 mL)
customdecanted again
dissolutionThe waxy solid was dissolved in methanol (50 mL)
filtrationfiltered
customto remove insoluble salts
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-8ceeefd2ff06415c9579861efdd54dcd
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08471005B2

Verknüpfte Notizen

Wird geladen…