Diethyl Ether → 17beta-Methoxy-2,2-dimethyl-5alpha-androstan-3-one

HRID 848776

Reaktionsgleichung

Reaktionsgleichung von HRID 848776
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:21])C[CH2:15]1)[CH2:10][CH2:9]3.C(N(CC)[CH:26]([CH3:28])[CH3:27])(C)C.CI.[CH2:33](OCC)C>CN(C=O)C.[Ag]=O>[CH3:33][O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:21])[C:26]([CH3:27])([CH3:28])[CH2:15]1)[CH2:10][CH2:9]3

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10635DihydrotestosteroneHCID 81531Diisopropylethylamine

Produkt 1

HCID 1283685117beta-Methoxy-2,2-dimethyl-5alpha-androstan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

17β-Hydroxy-5α-androstan-3-one (50 g.) in DMF (500 ml.) is cooled to 5° in an ice bath and silver oxide (58 g.) and N,N-diisopropylethylamine is added (85 ml.). The mixture is stirred and methyl iodide (142 g.) is slowly added keeping the temperature at about 5°. The stirring is continued and the mixture is allowed to come to 20°-25°. After 17 hours diethyl ether (2 l.) is added and the mixture filtered thru a bed of Celite to remove the inorganic solids. The filtrate is washed with water, dilute hydrochloric acid, water again, and dried over sodium sulfate, then filtered, and concentrated. The concentrate is column chromatographed over silica gel. The appropriate fractions (TLC) are pooled and concentrated to give the title compound, m.p. 116°-120°, IR (mull) 1700 cm-1 ; NMR (CDCl3) 0.77, 1.01, 1.08, 1.18, 3.24, and 3.37 δ.

Aufarbeitung

  1. customat about 5°
  2. customto come to 20°-25°
  3. filtrationthe mixture filtered
  4. customto remove the inorganic solids
  5. washThe filtrate is washed with water, dilute hydrochloric acid, water again
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed over silica gel
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d5003ad2bca4a1db324eaafd56502e2
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04297350

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