Dehydroepiandrosterone → 3Betabenzyloxycarbonyloxy-5androsten-17-one

HRID 581686

Reaktionsgleichung

Reaktionsgleichung von HRID 581686
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 5881DehydroepiandrosteroneHCID 10387Benzyl chloroformate

Produkt 1

HCID 542344703Betabenzyloxycarbonyloxy-5androsten-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of dehydroepiandrosterone (2.88 g, 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.

Aufarbeitung

  1. washthe mixture is washed with water
  2. customevaporated to dryness
  3. dissolutionThe residue is then dissolved in acetone
  4. customprecipitated in iced water
  5. waitAfter 16 h
  6. filtrationcrystals are filtered
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4968c1df4afc4f2ab752532e0962b788
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922700

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