Water → HCID 86660496, Verbindung

HRID 244251

Reaktionsgleichung

Reaktionsgleichung von HRID 244251
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20].[CH3:21][Mg]Br.O>C1COCC1.C(OCC)(=O)C>[CH3:21][C@@:3]1([OH:20])[CH2:4][CH2:5][C@H:6]2[C@H:7]3[C@H:17]([CH2:18][CH2:19][C@:2]12[CH3:1])[C@:15]1([CH3:16])[CH:10]([CH2:11][CH:12]=[CH:13][CH2:14]1)[CH2:9][CH2:8]3

Komponenten

6

Edukt 3

HCID 962WaterHCID 1019285alpha-Androst-2-en-17-oneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 86660496HCID 86660496, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound 2 (300 mg, 1.10 mmol) in anhydrous THF (15 mL) under an atmosphere of argon at 0° C. was added methyl magnesium bromide (1.4 M in THF; 945 μL, 1.32 mmol). The solution was allowed to return to room temperature and was subsequently stirred overnight. The solution was then diluted with ethyl acetate and poured into water. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by high performance flash chromatography (Biotage) using Hexanes/EtOAc (95:5) as eluant to yield compound 27 (123 mg, 39%). 1H NMR (CDCl3) δ: 0.78 (s, 18-CH3), 0.86 (s, 19-CH3), 1.21 (s, 17α-CH3), 0.65-2.05 (residual CH and CH2), 5.59 (m, 2×CH of alkene).

Aufarbeitung

  1. customto return to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude compound was purified by high performance flash chromatography (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-d6f793d5d1f64cca81c7bc349d2c5c27
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653054B2

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