Reacción #2175450

Ecuación de reacción

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

NaBH4

acetic acid

→

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

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente