Reacción #68086

Ecuación de reacción

hydrochloric acid

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

(2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde

sodium triacetoxyborohydride

→

ethyl 4-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate

Rendimiento 68.2%

Disolventes

water

chloroform

acetic acid

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   OtroThe organic layer was separated
4. 4
   workup.ADDITIONby adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer
5. 5
   Extracciónextracted with chloroform
6. 6
   Lavadowashed with aqueous saturated sodium chloride solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure
9. 9
   OtroThe residue thus obtained
10. 10
    Otrowas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Procedimiento

To 2.4 mL of dichloromethane solution containing 89 mg of ethyl 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate and 94 mg of (2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde, 24 μL of acetic acid was added and stirred at room temperature for 30 min. To the reaction mixture, 76 mg of sodium triacetoxyborohydride was added, and stirred at room temperature for 1 hour. To the reaction mixture, chloroform and water were added, and adjusted to pH 1 with 6 mol/L hydrochloric acid. The organic layer was separated, and adjusted to pH 13 by adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer, thereafter 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. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1], to give 87 mg of ethyl 4-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate as a colorless oil.

Fuente