Reaktion #52279

Reaktionsgleichung

7-Ethoxycarbonylmethyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Lithium borohydride

ammonium chloride

→

7-(2-hydroxy-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Ausbeute 49.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was refluxed overnight (16 h)
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   TrocknenThe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated under vacuum
6. 6
   Sonstigeto give a crude mixture, which
7. 7
   Sonstigewas purified via column chromatography

Vorschrift

7-Ethoxycarbonylmethyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (synthetic methodology described in Published International Patent Appl. WO 00/33838) (6.11 g, 19.0 mmol) was dissolved in tetrahydrofuran (40 mL) at room temperature. The solution was place under argon. Lithium borohydride [2M in tetrahydrofuran] (22.8 mmol, 11.43 mL) was carefully added and the reaction was refluxed overnight (16 h). The mixture was poured into a solution of saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and evaporated under vacuum to give a crude mixture, which was purified via column chromatography to give 7-(2-hydroxy-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (49% yield). 1H NMR (Cl3CD), δ 7.30 (d, 1H, J=7.6 Hz), 7.76 (d, 1H, J=7.6 Hz), 3.98 (m, 2H), 3.78 (m, 2H), 2.92 (m, 2H), 2.71 (m, 2H), 1.92 (m, 2H), 1.54 (s, 9H).

Quelle