反応 #60576

反応方程式

2-methoxy-estra-1,3,5(10)-triene-3,17β-diol

diethylamino sulfur trifluoride

→

17α-fluoro-3-hydroxy-2-methoxy-estra-1,3,5(10)-triene

収率 21.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他the cold bath was removed
2. 2
   workup.ADDITIONit was poured into aqueous sodium bicarbonate solution
3. 3
   抽出extracted with dichloromethane (3×)
4. 4
   その他The combined organic phases were dried
5. 5
   濃縮concentrated by evaporation in a rotary evaporator
6. 6
   その他Flash chromatography (cyclohexane/ethyl acetate=10:1) yielded 49% crude product, which
7. 7
   その他was purified by means of HPLC (Chiracel OD-H 250×4.6 mm; n-heptane/2-propanol=95/5)

実験手順

215 mg of 2-methoxy-estra-1,3,5(10)-triene-3,17β-diol was dissolved in 20 ml of absolute dichloromethane and cooled to −35° C. Then, 280 μl of diethylamino sulfur trifluoride was added, and the cold bath was removed. After 1 hour, it was poured into aqueous sodium bicarbonate solution and extracted with dichloromethane (3×). The combined organic phases were dried and concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate=10:1) yielded 49% crude product, which was purified by means of HPLC (Chiracel OD-H 250×4.6 mm; n-heptane/2-propanol=95/5). 46 mg (21%) of 17α-fluoro-3-hydroxy-2-methoxy-estra-1,3,5(10)-triene was obtained as colorless crystals.

出典