Reaktion #744052

Reaktionsgleichung

NaBH(OAc)3

(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

1,1-dimethylethyl 4-piperidinylcarbamate

NaHCO3

→

desired compound

Ausbeute 77.0%

1,1-Dimethylethyl {1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate

Ausbeute 77.0%

Lösungsmittel

chloroform

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
2. 2
   SonstigeThe combined organic phases were dried
3. 3
   Sonstigeevaporated
4. 4
   Sonstigethe crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient

Vorschrift

A mixture of (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (as the methyl hemiacetal) (1.09 g, 5.291 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (1.06 g, 5.291 mmol) in chloroform (50 ml) and MeOH (2.5 ml) was stirred for 2 h before addition of NaBH(OAc)3 (3.37 g, 15.873 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the desired compound (1.591 g, 77%).

Quelle