HCID 11001884, compound → HCID 12134979, compound

HRID 1750893Notes

Reaction equation

HRID 1750893 reaction equation
[OH:1][C:2]1[C:19]([CH:20]([CH3:23])[CH:21]=[CH2:22])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:24])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[C:19]([CH:20]([CH3:23])[CH2:21][CH3:22])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:24])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 11001884HCID 11001884, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12134979HCID 12134979, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the known 3-hydroxy-2-(1-methyl-2-propenyl)estra-1,3,5(10)-trien-17-one (ref. Patton, 1962; Chemical Abstracts Registry Number [98543-85-2], 30 mg, 0.093 mmol) dissolved in 10 mL of anhydrous ethanol was added 20 mg of 5% Pd/C. The reaction flask was shaken under 2.7 atm. of hydrogen for 3 h. The reaction mixture was then filtered and the catalyst was washed with ethanol. After solvent removal, the crude product was purified by chromatography (silica gel eluted with 12.5% ethyl acetate in hexanes) and then recrystallized from methylene chloride-hexanes to give 20 mg of pure product: m.p. 186-187° C.; 1H NMR(CDCl3) δ0.85-0.90 (m, 3H, CH3), 0.91 (s, 3 h CH3), 1.20-1.24 (m, 3H, CH3), 2.81-2.89 (m, 2H, CH2), 6.51 (s, 1H, Ar—H), 7.06 (s, 1H, Ar—H); 13C NMR(CDCl3) δ12.17, 13.75, 20.44, 21.46, 25.93, 28.91, 29.83, 31.49, 33.87, 35.81, 38.33, 44.05, 48.01, 50.24, 115.37, 123.99, 124.17, 130.86, 131.88, 134.78, 157.267, 221.79.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe catalyst was washed with ethanol
  3. customAfter solvent removal
  4. customthe crude product was purified by chromatography (silica gel eluted with 12.5% ethyl acetate in hexanes)
  5. customrecrystallized from methylene chloride-hexanes

Sources & evidence

ORD record
ord-0177e198967e4d4bbd14da1b5db02b80
Source dataset
uspto-grants-2015_10
Patent number
US09156876B2

Reaction notes

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