反応 #449983

ord-32042e3fd0384302addec26abafb0d89

反応方程式

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
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
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
product
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
C[N+]1([O-])CCOCC1
4-methyl morpholine N-oxide
→
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
7β-Methyl-5α-4-azapregnane-3,20-dione

反応物

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
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
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
product
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
C[N+]1([O-])CCOCC1
4-methyl morpholine N-oxide

試薬

CCC[N+](CCC)(CCC)CCC.[O]=[Ru](=[O])(=[O])[O-]
tetrapropylammonium perruthenate

溶媒

ClCCl
methylene chloride

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.ADDITIONthe reaction mixture was poured through pad of silica gel in a 300 mL sintered glass funnel which
  2. 2
    洗浄was subsequently eluted with 4:1 ethyl acetate/methylene chloride (5 L)
  3. 3
    その他The solvent was removed by rotoevaporation
  4. 4
    その他the title compound recrystallized

実験手順

To a stirred solution of 20-hydroxy-7β-methyl-5α-4-azapregnan-3-one (22.3 gms, 67 mmol, product of Step 10) in dry methylene chloride under nitrogen (110 mL) was added 4-methyl morpholine N-oxide (11.8 gms, 100 mmol) followed by 4 Å molecular sieves (33 gm). To this mixture was added tetrapropylammonium perruthenate (1.2 gm). After stirring at room temperature for 4 h, the reaction mixture was poured through pad of silica gel in a 300 mL sintered glass funnel which was subsequently eluted with 4:1 ethyl acetate/methylene chloride (5 L). The solvent was removed by rotoevaporation and the title compound recrystallized.

出典

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