Reaktion #744215

Reaktionsgleichung

[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

Lösungsmittel

MeOH CHCl3

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle