Реакция #93687

ord-bd5c729404b84367bff7d0d02b5a83a8

Уравнение реакции

CC(C)(C)[Si](C)(C)Cl
tert.-butyldimethylchlorosilane
C[C@]12CC[C@H](O)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one
c1c[nH]cn1
imidazole
→
CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@H](O)[C@H]3[C@@H]4[C@@H]5C[C@@H]5C(=O)[C@@]4(C)CC[C@@H]32)C1
3β-(tert.-butyldimethylsilyloxy)-7β-hydroxy-15β,16β-methylene-5-androsten-17-one
Выход 78.9%

Реактанты

CC(C)(C)[Si](C)(C)Cl
tert.-butyldimethylchlorosilane
C[C@]12CC[C@H](O)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one
c1c[nH]cn1
imidazole

Реагенты

Нет

Растворители

CN(C)C=O
dimethylformamide
CN(C)C=O
dimethylformamide

Условия реакции

Температура
-20°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThe reaction product is precipitated with sodium-chloride-
  2. 2
    workup.ADDITIONcontaining water
  3. 3
    Фильтрацияfiltered off
  4. 4
    Промывкаwashed with water
  5. 5
    workup.DISSOLUTIONdissolved in methylene chloride
  6. 6
    СушкаThe solution is dried over sodium sulfate
  7. 7
    Другоеevaporated

Методика

A solution of 120 g of 3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one in 1,000 ml of dimethylformamide is combined with 31 g of imidazole and cooled to -20° C. Within 2 hours, 63 g of tert.-butyldimethylchlorosilane in 450 ml of dimethylformamide is added dropwise to the reaction mixture, and the latter is agitated for another hour. The reaction product is precipitated with sodium-chloride-containing water, filtered off, washed with water, and dissolved in methylene chloride. The solution is dried over sodium sulfate and evaporated. After chromatography on silica gel with hexane-acetone, 128.8 g of 3β-(tert.-butyldimethylsilyloxy)-7β-hydroxy-15β,16β-methylene-5-androsten-17-one is obtained.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04614616uspto-grants-1986_09