Реакция #472710

Уравнение реакции

(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

tert-butyl (piperidin-4-yl)carbamate

sodium triacetoxyborohydride

sodium hydrogen carbonate

→

tert-butyl (1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Выход 81.7%

Растворители

dichloromethane

acetic acid

chloroform

Условия реакции

Обработка

1. 1
   Другоеthe organic layer was separated
2. 2
   Экстракцияthe aqueous layer was extracted with chloroform
3. 3
   Промывкаthe resultant solution was washed sequentially with water
4. 4
   Сушкаa saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   ДругоеThe resultant residue was purified by basic silica gel column chromatography

Методика

To a solution 0.16 g of (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde in 2 mL of dichloromethane, 0.14 g of tert-butyl (piperidin-4-yl)carbamate, 41 μL of acetic acid and 0.23 g of sodium triacetoxyborohydride were added, and the mixture was stirred at room temperature for 1 hour 30 minutes. The reaction mixture was charged with chloroform and a saturated aqueous sodium hydrogen carbonate solution and adjusted to pH 8.5, 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 sequentially with water and 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 basic silica gel column chromatography using an eluent of chloroform:methanol=19:1 to obtain 0.23 g of tert-butyl (1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oily substance.

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