تفاعل #68074

معادلة التفاعل

sodium hydrogen carbonate

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

2,3-dihydro(1,4)dioxino(2,3-c)pyridine-7-carbaldehyde

sodium triacetoxyborohydride

→

ethyl 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

المردود 58.0%

المذيبات

chloroform

water

acetic acid

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   درجة الحرارةcooling
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with aqueous saturated sodium chloride solution
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   أخرىthe solvent was removed under reduced pressure
7. 7
   أخرىThe residue thus obtained
8. 8
   أخرىwas purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]

الإجراء التجريبي

To 2 mL of dichloromethane solution containing 80 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 41 mg of 2,3-dihydro(1,4)dioxino(2,3-c)pyridine-7-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=20:1], to give 65 mg of ethyl 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate as a yellow oil.

المصدر