Reaktion #2175450

Reaktionsgleichung

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

NaBH4

acetic acid

→

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

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle