反应详情

1H-NMR (CDCl3) δ: 3.96 (3H, s), 5.13 (2H, s), 6.63 (1H, d, J=8.4 Hz), 6.70 (1H, d, J=9.8 Hz), 6.71 (1H, d, J=8.4 Hz), 7.45 (1H, t, J=8.4 Hz), 8.24 (1H, d, J=9.8 Hz), 9.66 (1H, s) (2) To 2.4 mL of dichloromethane solution containing 0.10 g of (5-methoxy-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 24 μL of acetic acid were added, and stirred for 20 min. To the reaction mixture, 0.15 g of sodium triacetoxyborohydride was added, and stirred for 50 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 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; hexane:ethyl acetate=1:3], to give 0.18 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale yellow oil.

1. additionwere added
2. stirringstirred for 50 min
3. customthe organic layer was separated
4. extractionthe aqueous layer was extracted with chloroform
5. washwashed with aqueous saturated sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was removed under reduced pressure
8. customThe residue thus obtained
9. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:3]