HCID 66651877, compound → HCID 66652075, compound

HRID 418939Notes

Reaction equation

HRID 418939 reaction equation
[C:1]([C:4]1[CH:17]=[C:16]2[C:7]([CH:8]3[CH:13]([CH:14]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[CH2:15]2)[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:6][C:5]=1[O:26][CH3:27])([CH3:3])=[CH2:2]>[Pd].O>[CH:1]([C:4]1[CH:17]=[C:16]2[C:7]([CH:8]3[CH:13]([CH:14]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH2:15]2)[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:6][C:5]=1[O:26][CH3:27])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66651877HCID 66651877, compound

Product 1

HCID 66652075HCID 66652075, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Combine 7-Isopropenyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (0.14 g, 0.39 mmol) and 10% Pd/C (0.13 g) and reduce at 50 psi of H2O.N. Filter catalyst and remove solvent in vacuo to yield the titled compound (0.13 g, 93%). 1H NMR (CDCl3): 7.28 (d, J=8.4 Hz, 2H), 7.02 (s, 1H), 6.92 (d, J=8.8 HZ, 2H), 6.89 (s, 1H), 3.87 (s, 3H), 3.85 (s, 3H), 3.25 (m, 4H), 2.85 (m, 1H), 2.5 (m, 1H), 2.06 (m, 1H), 1.8-1.1 (m, 13H).

Workup

  1. customFilter catalyst and remove solvent in vacuo

Sources & evidence

ORD record
ord-d49810ada1b8486a902440ed5fd622f9
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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