반응 #68117

반응 방정식

sodium hydrogen carbonate

(7-(difluoromethoxy)-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

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

sodium triacetoxyborohydride

→

tert-butyl (1-(2-(7-(difluoromethoxy)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

수율 0.1%

용매

chloroform

Water

acetic acid

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred for 40 min
3. 3
   기타the organic layer was separated
4. 4
   세척washed sequentially with water and aqueous saturated sodium chloride solution
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   기타The residue thus obtained
8. 8
   기타was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

실험 절차

To 1.5 mL of dichloromethane solution containing 0.12 g of (7-(difluoromethoxy)-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.16 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 15 μL of acetic acid were added, and stirred for 5 min. To the reaction mixture, 0.14 g of sodium triacetoxyborohydride was added, and stirred for 40 min. Water, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, 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; hexane:ethyl acetate=2:3], to give 0.19 mg of tert-butyl (1-(2-(7-(difluoromethoxy)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a colorless oil.

출처