Androstane-3beta,5alpha,17beta-triol → HCID 14135097, Verbindung

HRID 42083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42083
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@:10]4([OH:21])[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:22]>CS(C)=O>[OH:21][C@:10]12[CH2:11][C:12](=[O:20])[CH2:13][CH2:14][C@:15]1([CH3:16])[C@@H:17]1[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C:3](=[O:22])[CH2:4][CH2:5]3)[CH2:8][CH2:9]2

Komponenten

3

Edukt 1

HCID 14135090Androstane-3beta,5alpha,17beta-triol

Produkt 1

HCID 14135097HCID 14135097, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of androstane-3β,5α,17β-triol (0.48 g) and IBX (0.72 g) in DMSO (8 mL) was stirred at −15° C. overnight and then quenched at room temperature by addition of H2O (40 mL). After stirring for 15 min, the mixture was filtered and the cake was washed with EtOAc. The layers were separated, and the aqueous phase was extracted with EtOAc (3×40 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give the title compound II-aa (0.36 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.48 (1H, s), 2.72 (1H, d), 2.60-1.18 (20H, m), 1.23 (3H, s), 0.86 (3H, s).

Aufarbeitung

  1. customquenched at room temperature by addition of H2O (40 mL)
  2. filtrationthe mixture was filtered
  3. washthe cake was washed with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×40 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

Quellen und Nachweise

ORD-Eintrag
ord-31822fd4df274848ae06522671e37093
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536160B2

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