Cornforth reagent → 1-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone

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Reaktionsgleichung

[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH:34]([OH:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Pyridinium dichromate (4.0 g, 10.63 mmol) was added to a solution of 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol (0.5 g, 1.5 mmol) in dimethylformamide (25 ml) at 0° C. The resulting solution was stirred at 0° C. until the starting material was consumed and then quenched with water, basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over sodium sulfate. The residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes to give 1-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone (0.32 g) as an oil.

Aufarbeitung

customwas consumed
customquenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
customThe residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes

Quellen und Nachweise

ORD-Eintrag: ord-8b3df3d9cd414ab5be354de437c37ab4
Quelldatensatz: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06984637B2

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