Reaktion #744227

Reaktionsgleichung

sodium carbonate

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

sodium triacetoxyborohydride

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

→

title compound

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

Lösungsmittel

DCM

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred overnight
2. 2
   EinengenThe reaction mixture was concentrated

Vorschrift

Phenylmethyl {[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate (1.17 g; 4.560 mmol) and (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (as the methyl hemiacetal)) (855 mg, 4.17 mmol) were combined in anhydrous DCM (5 ml) and anhydrous MeOH (1 ml) with a spatula of solid sodium carbonate. The reaction mixture was stirred under nitrogen for 1 h then sodium triacetoxyborohydride (2.76 g; 12.44 mmol) was added and stirred overnight. The reaction mixture was concentrated and the title compound was obtained as a pale yellow oil (1.69 mg, 87%) after column:chromatography (90:10: DCM:MeOH).

Quelle