Реакция #68076

Уравнение реакции

sodium hydrogen carbonate

ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

2,3-dihydrobenzo(b)(1,4)dioxin-6-carbaldehyde

sodium triacetoxyborohydride

→

ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Выход 89.4%

Растворители

chloroform

water

acetic acid

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   Температураcooling
3. 3
   ДругоеThe organic layer was separated
4. 4
   Промывкаwashed with aqueous saturated sodium chloride solution
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was removed under reduced pressure
7. 7
   ДругоеThe residue thus obtained
8. 8
   Другоеwas purified by silica gel column chromatography [eluent; chloroform:methanol=15:1]

Методика

To 2 mL of dichloromethane solution containing 80 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 40 mg of 2,3-dihydrobenzo(b)(1,4)dioxin-6-carbaldehyde and 14 μL of acetic acid were added at room temperature, 78 mg of sodium triacetoxyborohydride was added under ice-cooling, and stirred at room temperature for 1 hour. To the reaction mixture, water, chloroform and aqueous saturated sodium hydrogen carbonate solution 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 silica gel column chromatography [eluent; chloroform:methanol=15:1], to give 0.10 g of ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate as a yellow oil.

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