반응 #2175450

반응 방정식

9-Formyl-2,7-di(Boc-amino)fluorene

NaBH4

acetic acid

→

9-hydroxymethyl-2,7-di(Boc-amino)fluorene

용매

methanol

water

반응 조건

후처리

1. 1
   추출The reaction was extracted with ethyl acetate (2×100 mL)
2. 2
   세척the organic layers were washed with saturated NaHCO3 (4×20 mL) and brine (3×20 mL)
3. 3
   건조The organic layers were dried over MgSO4
4. 4
   여과filtered
5. 5
   기타evaporated
6. 6
   기타The crude product, orange solid, was purified by flash chromatography
7. 7
   세척silica gel 60 Å gradient elution 1-5% methanol in chloroform (alternative gradient elution with 15-20% ethyl acetate in dichloromethane, “DCM”)

실험 절차

9-Formyl-2,7-di(Boc-amino)fluorene (0.47 g, 1.1 mmol) was dissolved in anhydrous methanol (MeOH) (5 mL) under an argon atmosphere. NaBH4 (1.2 eq, 1.3 mmol, 0.05 g) was added and the reaction was stirred at room temperature for five hours. The reaction was diluted with deionized water and acidified to pH 5 with glacial acetic acid. The reaction was extracted with ethyl acetate (2×100 mL) and the organic layers were washed with saturated NaHCO3 (4×20 mL) and brine (3×20 mL). The organic layers were dried over MgSO4, filtered and evaporated. The crude product, orange solid, was purified by flash chromatography: silica gel 60 Å gradient elution 1-5% methanol in chloroform (alternative gradient elution with 15-20% ethyl acetate in dichloromethane, “DCM”). Product was a yellow solid (0.39, 83%). 1H-NMR (CD3OD): δ (ppm) 7.9 (s, 0.5H, NH urethane); 7.7 (s, 2H, Ar); 7.6 (d, 2H, Ar); 7.4 (d, 2H, Ar); 4.0 (m, 1H, CH); 3.9 (m, 2H, CH2); 1.6 (s, 18H, Boc).

출처