反応 #449981

ord-1eedab24260746c5840d835b610c2253

反応方程式

CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[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=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene
→
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
title compound
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

反応物

CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene
CC(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](C)C=C4NCCC[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=C4NCCC[C@]4(C)[C@H]3CC[C@]12C
20-tert-Butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene

試薬

[O]=[Pt]
platinum oxide

溶媒

CC(=O)O
acetic acid

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過The reaction mixture was filtered through a pad of Celite™
  2. 2
    ろ過filter aid (trademark for diatomaceous earth)
  3. 3
    その他to remove all of the acetic acid
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in chloroform
  5. 5
    ろ過filtered again through a pad of Celite™
  6. 6
    ろ過filter aid
  7. 7
    その他to remove residual catalyst
  8. 8
    その他The solvent was removed by roto-evaporation

実験手順

To a solution of 20-tert-butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene (23.9 g, 53.6 mmol, product of Step 8) in acetic acid (250 mL) was added platinum oxide (1.8 gm). The mixture was stirred overnight under hydrogen (1 atmosphere). The reaction mixture was filtered through a pad of Celite™ filter aid (trademark for diatomaceous earth) and the filtrate was coevaporated with toluene (3×500 mL) to remove all of the acetic acid. The residue was dissolved in chloroform and filtered again through a pad of Celite™ filter aid to remove residual catalyst. The solvent was removed by roto-evaporation to yield the title compound which was taken directly on to the next step without any further purification.

出典

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