Reaktion #618330

Reaktionsgleichung

2-Cyclopropyl-5-ethoxy-2′,4′-difluorobiphenyl-4-carbaldehyde

Ethyl 5-oxo-6-(piperidin-4-yl)-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate dihydrochloride monohydrate

Sodium triacetoxyborohydride

sodium hydrogen carbonate

→

title compound

Ausbeute 91.0%

Ethyl 6-(1-((2-cyclopropyl-5-ethoxy-2′,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate

Ausbeute 91.0%

Lösungsmittel

triethylamine

THF

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for overnight
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate (1.35 L)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Vorschrift

To a suspension of Ethyl 5-oxo-6-(piperidin-4-yl)-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate dihydrochloride monohydrate (10.1 g) in THF (203 mL) was added triethylamine (6.49 mL). The mixture was stirred for 30 minutes. 2-Cyclopropyl-5-ethoxy-2′,4′-difluorobiphenyl-4-carbaldehyde (7.73 g) was added to the mixture. The mixture was stirred for 30 minutes. Then Sodium triacetoxyborohydride (7.39 g) and acetic acid (1.33 mL) was added to the reaction mixture. The mixture was stirred at room temperature for overnight. The mixture was added to aqueous saturated sodium hydrogen carbonate solution (135 mL) and water (135 mL) at room temperature. The mixture was extracted with ethyl acetate (1.35 L). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (13.3 g).

Quelle