Реакция #744215

Уравнение реакции

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

phenylmethyl {[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Na2SO4

Na(OAc)3BH

→

Phenylmethyl [((3S,4S)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Растворители

MeOH CHCl3

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe solution stirred an additional 2 hours
2. 2
   КонцентрированиеThe reaction mixture was concentrated onto silica gel
3. 3
   Другоеchromatographed on a silica gel column [0-100% CHCl3/(90:10:1) CHCl3/MeOH/NH4OH)]
4. 4
   Другоеto yield a colorless oil

Методика

To a solution of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (0.654 g, 3.0 mmol) in 1:1 (MeOH/CHCl3) (50 mL) were added phenylmethyl {[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate (0.750 g, 3.0 mmol) and Na2SO4 (0.100 g) and the resulting solution stirred at ambient temperature for 18 hours. Na(OAc)3BH (1.91 g, 9.0 mmol) was added and the solution stirred an additional 2 hours. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column [0-100% CHCl3/(90:10:1) CHCl3/MeOH/NH4OH)] to yield a colorless oil. (0.897 g, 66%).

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