Реакция #744244

Уравнение реакции

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

1,1-dimethylethyl [(2R)-2-morpholinyl-methyl]carbamate

Na2SO4

Na(OAc)3BH

→

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

Растворители

MeOH CHCl3

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe solution stirred an additional 2 g
2. 2
   КонцентрированиеThe reaction mixture was concentrated onto silica gel
3. 3
   Другоеchromatographed on a silica gel column) [0-100% Hexanes/EtOAc]
4. 4
   Другоеto yield a yellowish oil

Методика

To a solution of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (0.500 g, 2.29 mmol) in 1:1 (MeOH/CHCl3) (25 mL) were added 1,1-dimethylethyl [(2R)-2-morpholinyl-methyl]carbamate (0.500 g, 2.29 mmol) and Na2SO4 (0.100 g) and the resulting solution stirred at ambient temperature for 18 h. Na(OAc)3BH (1.46 g, 6.87 mmol) was added and the solution stirred an additional 2 g. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column) [0-100% Hexanes/EtOAc] to yield a yellowish oil. (0.460 g, 48%)

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