反応 #449982

ord-9865a37380e546368ba5708807aebdf3

反応方程式

O=C([O-])O.[Na+]
sodium bicarbonate
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
product
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
F
hydrofluoric acid
→
CC(O)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
title compound
CC(O)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
20-Hydroxy-7β-methyl-5α-4-azapregnan-3-one

反応物

O=C([O-])O.[Na+]
sodium bicarbonate
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
product
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C[C@H]4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane
F
hydrofluoric acid

試薬

なし

溶媒

CC#N
acetonitrile

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度the reaction mixture was cooled to 0° C.
  2. 2
    抽出The mixture was extracted with methylene chloride (3×500 mL)
  3. 3
    洗浄the combined extracts washed with water, saturated salt solution
  4. 4
    乾燥dried over anhydrous sodium sulfate
  5. 5
    その他The solvent was removed by rotoevaporation

実験手順

To a slurry of crude 20-tert-butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane (25.2 g, product of Step 9) in acetonitrile (300 mL) was added an aqueous solution of hydrofluoric acid (12 mL). After stirring for 8 hr at room temperature, the reaction mixture was cooled to 0° C. and saturated sodium bicarbonate solution was slowly added. The mixture was extracted with methylene chloride (3×500 mL) and the combined extracts washed with water, saturated salt solution and dried over anhydrous sodium sulfate. The solvent was removed by rotoevaporation to give the title compound which was used without purification in the subsequent reaction.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05872126uspto-grants-1999_02