Reaktion #73836

Reaktionsgleichung

4-chloro-3-fluorophenylmagnesium bromide

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

ammonium chloride

→

title compound

Ausbeute 30.4%

4-(4-Chloro-3-fluoro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Ausbeute 30.4%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic solvent was removed in vacuo
2. 2
   ExtraktionThe mixture was extracted with ethyl acetate
3. 3
   Waschenthis extract was washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto afford a residue which
8. 8
   Sonstigewas purified by column chromatography (SiO2)
9. 9
   Wascheneluting with gradient of ethyl acetate/petrol (0% to 20%)

Vorschrift

A solution of 4-chloro-3-fluorophenylmagnesium bromide (15 ml, 7.5 mmol, 0.5M in THF) was added, under nitrogen, to 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.1 mmol). After 24 hours, saturated ammonium chloride solution was added then the organic solvent was removed in vacuo. The mixture was extracted with ethyl acetate, then this extract was washed with brine, dried (MgSO4), filtered and concentrated to afford a residue which was purified by column chromatography (SiO2), eluting with gradient of ethyl acetate/petrol (0% to 20%) to afford the title compound (511 mg, 30%). 1H NMR (Me-d3-OD) δ 1.48 (9H, s), 1.67 (2H, br.d), 1.92 (2H, td), 3.16-3.29 (2H, m), 3.99 (2H, br.d), 7.27 (1H, dd), 7.38 (1H, dd), 7.42 (1H, t).

Quelle