反応 #68148

反応方程式

sodium hydrogen carbonate

methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxylate

1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine

sodium triacetoxyborohydride

→

methyl 1-(2-(1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamino)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

収率 70.5%

溶媒

acetic acid

chloroform

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred for 0.5 hours
3. 3
   その他the organic layer was separated
4. 4
   洗浄The organic layer was washed with aqueous saturated sodium chloride solution
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   その他the solvent was removed under reduced pressure
7. 7
   その他The residue thus obtained
8. 8
   その他was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=3:1]

実験手順

To 10 mL of a chloroform solution containing 111 mg of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxylate and 93 mg of 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine, 23 μL of acetic acid was added and stirred at room temperature for 1 hour. To the reaction mixture, 132 mg of sodium triacetoxyborohydride was added and stirred for 0.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added and the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=3:1], to give 134 mg of methyl 1-(2-(1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamino)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate.

出典