Реакция #744077

Уравнение реакции

NaBH(OAc)3

NaHCO3

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

1,1-dimethylethyl 4-piperidinylcarbamate

→

desired compound

Выход 78.0%

1,1-Dimethylethyl (1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)carbamate

Выход 78.0%

Растворители

water

chloroform

MeOH

Условия реакции

Обработка

1. 1
   ЭкстракцияThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
2. 2
   ДругоеThe combined organic phases were dried
3. 3
   Другоеevaporated
4. 4
   Другоеthe crude residue purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

Методика

A mixture of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (3.807 g, 17.463 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (3.493 g, 17.463 mmol) in chloroform (100 ml) and MeOH (5 ml) was stirred for 1 h before addition of NaBH(OAc)3 (11.11 g, 52.39 mmol). The reaction was stirred for 0.5 h before addition of water (100 ml) and sat. aq NaHCO3 (100 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (5.453 g, 78%).

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