反応 #2766

ord-40b377d619b3445095890b35e71e45d2

反応方程式

CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3-acetoxy-androst-5-en-17-one
[BH4-].[Na+]
sodium borohydride
CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)CC[C@@H]32)C1
crude title compound
CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)CC[C@@H]32)C1
3-Acetoxy-Androst-5-en-17-ol

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.STIRRINGAfter the reaction mixture was stirred for one and 1/2 hours
  2. 2
    その他the ethanol solvent removed under vacuum
  3. 3
    抽出the residue extracted with ethyl acetate
  4. 4
    洗浄The organic layer was washed with aqueous Na2CO3, brine
  5. 5
    乾燥dried over sodium sulfate
  6. 6
    濃縮concentrated

実験手順

To a solution of 100 mg. (0.303 mmol) of 3-acetoxy-androst-5-en-17-one in 3 ml EtOH at -10° C., was added 22.9 mg (0.606 mmol) of sodium borohydride with stirring. After the reaction mixture was stirred for one and 1/2 hours, the mixture was diluted with 10 ml water, the ethanol solvent removed under vacuum, and the residue extracted with ethyl acetate. The organic layer was washed with aqueous Na2CO3, brine, dried over sodium sulfate and concentrated to leave a residue of crude title compound. Proton NMR confirmed the assigned structure.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05730964uspto-grants-1998_03