Acetic Acid → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

HRID 418944Notes

Reaction equation

HRID 418944 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:11]([CH:12]3[CH:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:10][C:9]([O:27][CH3:28])=[CH:8][CH:7]=2)=[O:4].C(O)(=O)C.CO.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([O:27][CH3:28])[CH:10]=2)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 666519606-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthren-9-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 666520266-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthren-9-carboxylic acid methyl ester (10.06 g, 26.6 mmol), 10% Pd—C (1.014 g), acetic acid (100 mL), methanol (150 mL), and ethyl acetate (150 mL), and stir under 100 psi of hydrogen atmosphere at 50° C. After 18 hours, filter reaction through Celite using ethyl acetate and concentrate to yield the titled compound (9.97 g, 99%) as a white solid. TLC Rf=0.25 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.28 (m, 1H), 7.22 (d, 2H, J=8.8 Hz), 6.98 (d, 1H, J=2.2 Hz), 6.84 (d, 2H, J=8.8 Hz), 6.80 (d, 1H, J=2.6 Hz), 4.33 (d, 1H, J=7.9 Hz), 3.86 (s, 3H), 3.82 (s, 3H), 3.55 (m, 1H), 3.51 (s, 3H), 3.06 (m, 1H), 2.36 (m, 2H), 1.78 (m, 3H), 1.38 (m, 4H).

Workup

  1. filtrationfilter
  2. customreaction through Celite
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-0190caba33404fd29e45ecef32e225a8
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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