Reaktion #8842

Reaktionsgleichung

methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Jones reagent

→

title compound

4-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction mixture was concentrated
2. 2
   Extraktiondiethyl ether and extracted three times with diethyl ether
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

To a solution of methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (23.0 g, 0.0734 mol) from Step C in acetone (775 mL) at room temperature was added Jones reagent (28.2 mL, 2.6M) via syringe. After 5 min, the reaction mixture was concentrated. The residue was taken up in water and diethyl ether and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (23.4 g) which was used in the next step without further purification.

Quelle