反応 #2175450

反応方程式

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

NaBH4

acetic acid

→

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

溶媒

methanol

water

反応条件

後処理

1. 1
   抽出The reaction was extracted with ethyl acetate (2×100 mL)
2. 2
   洗浄the organic layers were washed with saturated NaHCO3 (4×20 mL) and brine (3×20 mL)
3. 3
   乾燥The organic layers were dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated
6. 6
   その他The crude product, orange solid, was purified by flash chromatography
7. 7
   洗浄silica gel 60 Å gradient elution 1-5% methanol in chloroform (alternative gradient elution with 15-20% ethyl acetate in dichloromethane, “DCM”)

実験手順

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).

出典