Reaktion #2079

ord-1079585e7a194106a0429ed7ca89727f

Reaktionsgleichung

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate
→
C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-benzyloxycarbonyloxy-5-androsten-17-one

Edukte

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenthe mixture is washed with water
  2. 2
    Sonstigeevaporated to dryness
  3. 3
    workup.DISSOLUTIONThe residue is then dissolved in acetone
  4. 4
    Sonstigeprecipitated in iced water
  5. 5
    workup.WAITAfter 16 h
  6. 6
    Filtrationcrystals are filtered
  7. 7
    Sonstigedried in vacuo

Vorschrift

To a stirred solution of dehydroepiandrosterone (2.88 % 10 mmol) in methylene chloride (100 mL) is added dropwise benzylchloroformate, over a period of 30 min following the known procedure (F. Reber and T. Reichstein, Helv. Chim. Acta, 28, 1164, 1945). After stirring for 3 h, the mixture is washed with water and evaporated to dryness. The residue is then dissolved in acetone and precipitated in iced water. After 16 h, crystals are filtered and dried in vacuo.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728688uspto-grants-1998_03