Reaktion #620299

Reaktionsgleichung

4-[2-(5-bromo-2-chloro-pyridin-4-yl)-1-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

racemic 2-(di-tert-butylphosphino)-1,1′-binaphthyl

cesium carbonate

ethyl acetate

→

title compound

4-(5-Chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Sonstigethe organic phase is separated
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→50:50)

Vorschrift

A mixture of 4-[2-(5-bromo-2-chloro-pyridin-4-yl)-1-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (11.60 g), palladium acetate (500 mg), racemic 2-(di-tert-butylphosphino)-1,1′-binaphthyl (1.00 g), and cesium carbonate (14.00 g) in toluene (150 mL) is heated in an oil bath at 110° C. under argon atmosphere for 5 h. After cooling to room temperature, ethyl acetate and water are added and the organic phase is separated, washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→50:50) to give the title compound. LC (method 3): tR=1.44 min; Mass spectrum (ESI+): m/z=339 [M+H]+.

Quelle