반응 #68056

반응 방정식

sodium hydrogen carbonate

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

(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

sodium triacetoxyborohydride

→

tert-butyl (1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

수율 53.4%

용매

Chloroform

acetic acid

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at the same temperature for 30 min
3. 3
   기타the organic layer was separated
4. 4
   추출the aqueous layer was extracted with chloroform
5. 5
   세척washed sequentially with water and aqueous saturated sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   기타The residue thus obtained
9. 9
   기타was purified by silica gel column chromatography [eluent; ethyl acetate]

실험 절차

To 5 mL of dichloromethane solution containing 0.18 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 0.15 g of (5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde and 29 μL of acetic acid were added and stirred at room temperature for 1 hour. To the reaction mixture, 0.16 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and 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; ethyl acetate] to give 0.17 g of tert-butyl (1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a light brown foam.

출처