Estrone → (8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

HRID 1243298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243298
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:27]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 5870EstroneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of oestrone (3.35 g, 12.39 mmol) in DMF (50 ml) were added potassium carbonate (3.45 g, 25 mmol) and benzyl bromide (2.25 ml, 18.75 mmol) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred for 24 h, then quenched with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (MgSO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was triturated with Et2O, filtered and evaporated to afford 3.48 g (78% yield) of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 as a white solid.

Aufarbeitung

  1. customquenched with H2O
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was triturated with Et2O
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-25df7e296b534f039be29a4db2696a85
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119081B2

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