Water → 1alpha,3beta-Bis(triethylsilyloxy)-5-androsten-17-one

HRID 329535

Reaktionsgleichung

Reaktionsgleichung von HRID 329535
[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][C@H:16]([OH:21])[C@:15]3([CH3:22])[C@H:5]1[CH2:4][CH2:3]2.C(N([CH2:28][CH3:29])CC)C.[CH2:30]([Si:32]([CH2:36][CH3:37])([CH2:34][CH3:35])Cl)[CH3:31].O>N1C=CC=CC=1>[CH2:30]([Si:32]([CH2:28][CH3:29])([CH2:34][CH3:35])[O:21][C@@H:16]1[C@@:15]2([CH3:22])[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][C@@H:18]([O:20][Si:32]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:30][CH3:31])[CH2:17]1)[CH3:31]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 1679551-Hydroxydehydroepiandrosterone

Produkt 1

HCID 139854691alpha,3beta-Bis(triethylsilyloxy)-5-androsten-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In 600 ml of pyridine, 9.13 g of 1α-hydroxydehydroepiandrosterone was suspended. Under an argon stream, 100 ml of triethylamine and 39.0 g of triethyl chlorosilane were added to the suspension, and the mixture was stirred for 24 hours at room temperature. After adding 500 ml of water, the solvent was distilled off under vacuum. The residue was subjected to extraction with benzene. The benzene layer was successively washed with an aqueous solution of 0.5N HCl, water, saturated sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The residue obtained by distilling off the solvent under vacuum was subjected to silica gel column chromatography and eluted with chloroform, whereby 9.64 g of 1α,3β-bis(triethylsilyloxy)-5-androsten-17-one was obtained as a pale yellow crystal. Part of the compound was recrystallized from methanol to give colorless needles having a melting point of 99°-100° C.

Aufarbeitung

  1. distillationthe solvent was distilled off under vacuum
  2. extractionThe residue was subjected to extraction with benzene
  3. washThe benzene layer was successively washed with an aqueous solution of 0.5N HCl, water, saturated sodium hydrogencarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under vacuum
  7. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-9ea832c1589043b0a35108158ab39074
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891364

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