تفاعل #2175450

معادلة التفاعل

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

NaBH4

acetic acid

→

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

المذيبات

methanol

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر