6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418955
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[C:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[H][H]>[Pd].C(O)(=O)C.CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH3:17])[CH:12]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 2

HCID 666520386-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthreneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 666519736-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 18673759MeOH THF HOAcLösungsmittel

Versuchsvorschrift

Combine 6-methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene (0.116 g, 0.347 mmol), Pd-Black (14.7 mg, 0.139 mmol) and acetic acid/methanol/tetrahydrofuran (1.0 mL, 10.0 mL, 3.0 mL) at 50 psi Hydrogen pressure. After 18 hours, filter off the Pd catalyst over celite eluting with ethyl acetate. Concentrate and flash chromatograph with 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.108 g, 93%) as a clear oil. TLC Rf=0.30 in 5:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.26 (d, 1H, J=8.4 Hz), 7.03 (m, 3H), 6.83 (m, 3H), 3.90 (s, 3H), 3.83 (s, 3H), 3.36 (m, 2H), 3.12 (m, 1H), 2.52 (m, 1H), 2.35 (m, 1H), 1.87 (m, 1H), 1.51 (m, 4H), 1.30 (m, 2H), 1.18 (d, 3H, J=6.6 Hz).

Aufarbeitung

  1. filtrationfilter off the Pd catalyst over celite
  2. washeluting with ethyl acetate
  3. concentrationConcentrate

Quellen und Nachweise

ORD-Eintrag
ord-7e842b54ec34499998abc1e5be7b152e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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