Reaktion #58449

Reaktionsgleichung

(RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)piperidine

ammonium chloride

2-(4-fluorophenyl)-furan

n-butyl lithium

→

title compound

Ausbeute 86.6%

(RS)-1-(tert-butyloxycarbonyl)-2-((5-(4fluorophenyl)-furan-2-yl)carbonyl)piperidine

Ausbeute 86.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×50 ml)
2. 2
   WaschenThe combined organics were washed with saturated aqueous sodium hydrogen carbonate (50 ml)
3. 3
   Sonstigeevaporated in vacuo
4. 4
   SonstigeThe residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane

Vorschrift

To a stirred solution of 2-(4-fluorophenyl)-furan (1.8 g, 11.1 mmol) in THF (100 ml) at −35° C. was added n-butyl lithium (2.5M in THF) (4.54 ml, 11.4 mmol) over 3 min. The resultant mixture was stirred for 10 min. at −35° C. and then (RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)piperidine (3.09 g, 11.4 mmol) in THF (10 ml) was added over 1 min. The resultant solution was stirred for 15 min. at −35° C. and then poured into saturated ammonium chloride (120 ml) and extracted with ethyl acetate (3×50 ml). The combined organics were washed with saturated aqueous sodium hydrogen carbonate (50 ml) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a golden oil (3.59 g, 85%).

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