反応 #68131

反応方程式

sodium cyanoborohydride

(2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine

sodium hydrogen carbonate

1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile

→

4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile

収率 44.7%

1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

収率 44.7%

溶媒

dichloromethane

ethanol

acetic acid

chloroform

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirred at the same temperature for 15 min
4. 4
   その他the organic layer was separated
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
8. 8
   その他The residue thus obtained
9. 9
   その他was purified by flash silica gel column chromatography [hexane:ethyl acetate=4:1]

実験手順

To a mixture of 3 mL of ethanol and 3 mL of dichloromethane solution containing 0.18 g of 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile, 1 mL of ethanol solution containing 0.13 g of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 0.30 g of molecular sieves 3A, and 45 μL of acetic acid were added at room temperature. After stirred at 40° C. for 1.5 hours, the mixture was cooled to the room temperature, 36 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 15 min. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, 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 flash silica gel column chromatography [hexane:ethyl acetate=4:1], to give (A) 36 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a colorless oil and (B) 0.11 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a white foam.

出典