反応 #68049

反応方程式

methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

trifluoroacetic acid

→

methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-3-carboxylate

収率 138.0%

反応条件

後処理

1. 1
   その他The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and chloroform
2. 2
   workup.ADDITIONwere added
3. 3
   その他The organic layer was separated
4. 4
   抽出the aqueous layer was extracted with chloroform
5. 5
   洗浄washed with aqueous saturated sodium chloride solution
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   その他the solvent was removed under reduced pressure

実験手順

To 0.37 g of methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, 2 mL of 90% aqueous trifluoroacetic acid solution was added and stirred for 4 hours. The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.44 g of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-3-carboxylate. (2) To 5 mL of a dichloromethane solution containing 0.44 g of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-3-carboxylate, 0.46 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 60 μL of acetic acid were added and stirred for 1 hour. To the reaction mixture, 0.37 g of sodium triacetoxyborohydride was added and stirred for 2 hours. Chloroform and water were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.31 g of methyl 1-(2-(4-((tert-butoxycarbonyl) (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate as a yellow oil.

出典