반응 #52279

반응 방정식

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

수율 49.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the reaction was refluxed overnight (16 h)
2. 2
   추출extracted with ethyl acetate
3. 3
   건조The organic layer was dried over Na2SO4
4. 4
   여과filtered
5. 5
   기타evaporated under vacuum
6. 6
   기타to give a crude mixture, which
7. 7
   기타was purified via column chromatography

실험 절차

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).

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