반응 #472804

반응 방정식

tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate

(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

sodium triacetoxyborohydride

sodium hydrogen carbonate

→

tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate

수율 59.5%

용매

dichloromethane

acetic acid

chloroform

반응 조건

후처리

1. 1
   기타the organic layer was separated
2. 2
   추출the aqueous layer was extracted with chloroform
3. 3
   세척the resultant solution was washed with a saturated aqueous sodium chloride solution
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   기타The resultant residue was purified by flash basic silica gel column chromatography

실험 절차

To a solution of 0.16 g of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate in 3 mL of dichloromethane, 0.10 g of (6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde, 26 μL of acetic acid and 0.15 g of sodium triacetoxyborohydride were added, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash basic silica gel column chromatography using an eluent of chloroform to obtain 0.15 g of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate as a light brown oily substance.

출처