Reaktion #1597913

Reaktionsgleichung

sodium hydrogen carbonate

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

tert-butyl(piperidin-4-yl)carbamate

sodium triacetoxyborohydride

→

tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Ausbeute 18.8%

Lösungsmittel

chloroform

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 10 hours
2. 2
   Sonstigethe organic layer was separated
3. 3
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   workup.ADDITIONEthanol was added to the resultant residue
7. 7
   Filtrationthe solid was filtered off

Vorschrift

To a solution of 1.66 g of (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde in 42 mL of chloroform, 1.61 g of tert-butyl(piperidin-4-yl)carbamate and 0.48 g of acetic acid were added, and the mixture was stirred at room temperature for 7.5 hours. To the reaction mixture, 2.56 g of sodium triacetoxyborohydride was added, and the mixture was stirred for 10 hours. Thereto was added a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Ethanol was added to the resultant residue, and the solid was filtered off to obtain 0.59 g of tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Quelle