Reaktion #57368

Reaktionsgleichung

Ethyl acetate

(MeSO2)2O

methyl 4-(4-fluorophenyl)-2-isopropyl-5,6,7,8-tetrahydro-[1,8]naphthyridine-3-carboxylate

3,5-lutidine

→

methyl 4-(4-fluorophenyl)-2-isopropyl-8-methanesulfonyl-5,6,7,8-tetrahydro-[1,8]naphthyridine-3-carboxylate

Ausbeute 86.1%

Lösungsmittel

H2O

CH2Cl2

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting two phases were separated
2. 2
   WaschenThe organic phase was washed with aqueous NaHCO3 (5%, 50 mL)
3. 3
   SonstigeThe solvent was removed under reduced pressure
4. 4
   Sonstigeto afford a yellowish oil which
5. 5
   SonstigeThe crude material was recrystallized from i-PrOH/H2O (85:15, 45 mL)

Vorschrift

A solution of (MeSO2)2O (15.9 g, 0.091 mol) in anhydrous CH2Cl2 (50 mL) was added to a solution of Part C methyl 4-(4-fluorophenyl)-2-isopropyl-5,6,7,8-tetrahydro-[1,8]naphthyridine-3-carboxylate (10. g, 0.030 mol) and 3,5-lutidine (20.9 mL, 0.182 mol) in anhydrous toluene (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 days. Ethyl acetate (200 mL) and H2O (50 mL) were added, and the resulting two phases were separated. The organic phase was washed with aqueous NaHCO3 (5%, 50 mL), followed by half-saturated brine (50 mL). The solvent was removed under reduced pressure to afford a yellowish oil which solidified slowly. The crude material was recrystallized from i-PrOH/H2O (85:15, 45 mL) to afford 10.5 g (85% yield) of methyl 4-(4-fluorophenyl)-2-isopropyl-8-methanesulfonyl-5,6,7,8-tetrahydro-[1,8]naphthyridine-3-carboxylate as a off-white solid.

Quelle