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

HRID 418898Notes

Reaction equation

HRID 418898 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.C(O)C>[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 702EthanolHCID 666519406-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthrene

Product 1

HCID 666521086-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthrene (48.5 mg, 0.15 mmol), 10% Pd—C (5.4 mg, 0.04 mmol), and ethanol (3 mL) and tetrahydrofuran (3 mL), degas, and add H2 at atmospheric pressure and at room temperature. After 18 hours, filter off the Pd catalyst over celite eluting with ethyl acetate. Concentrate and flash chromatograph with 0% to 20% ethyl acetate/hexanes to yield the titled compound (42.4 mg, 87%) as a clear oil. TLC Rf=0.51 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.25 (d, 2H, J=8.4 Hz), 7.11 (d, 1H, J=8.4 Hz), 6.97 (m, 1H), 6.90 (d, 2H, J=7.9 Hz), 6.75 (m, 1H), 3.82 (m, 6H), 3.19 (m, 3H), 2.87 (dd, 1H, J=15.0, 4.0 Hz), 2.49 (m, 1H), 2.04 (m, 1H), 1.65 (m, 2H), 1.45 (m, 1H), 1.29 (m, 1H), 1.15 (m, 3H).

Workup

  1. additionadd H2 at atmospheric pressure
  2. customat room temperature
  3. filtrationfilter off the Pd catalyst over celite
  4. washeluting with ethyl acetate
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-100a28c4102d412bab8715fcea173467
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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