반응 #68094

반응 방정식

sodium hydrogen carbonate

sodium cyanoborohydride

sodium cyanoborohydride

N-cyclopropyl-7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxamide

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate

→

tert-butyl (1-(2-(4-((cyclopropylamino)carbonyl)-7-methoxy-2-oxoquinolin-1-(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

수율 47.5%

용매

chloroform

methanol

acetic acid

methanol

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.STIRRINGstirred at the same temperature for 2 hours
3. 3
   workup.STIRRINGstirred at the same temperature for 2 hours and 15 min
4. 4
   workup.STIRRINGstirred at the same temperature for 2 hours
5. 5
   온도cooling
6. 6
   workup.ADDITIONwere added
7. 7
   기타the organic layer was separated
8. 8
   추출the aqueous layer was extracted with chloroform
9. 9
   세척washed with aqueous saturated sodium chloride solution
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    기타the solvent was removed under reduced pressure
12. 12
    기타The residue thus obtained
13. 13
    기타was purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30]

실험 절차

To 1.0 mL of methanol solution containing 0.13 g of N-cyclopropyl-7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxamide, 0.16 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 25 μL of acetic acid were added at room temperature and stirred at the same temperature for 1.5 hours. To the reaction mixture, 42 mg of sodium cyanoborohydride was added and stirred at the same temperature for 2 hours. Further, 42 mg of sodium cyanoborohydride was added and stirred at the same temperature for 2 hours and 15 min. 76 μL of acetic acid was added and stirred at the same temperature for 2 hours. To the mixture, aqueous saturated sodium hydrogen carbonate solution was added under ice-cooling to be adjusted to pH 8.7, 5.0 mL of methanol and 15 mL of chloroform were added, the organic layer was separated, and the aqueous layer was 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 flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30], to give 0.13 g of tert-butyl (1-(2-(4-((cyclopropylamino)carbonyl)-7-methoxy-2-oxoquinolin-1-(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a white foam.

출처