3-Hydroxy-17-methyleneestra-1,3,5(10)-triene-2-carboxaldehyde → 3-Hydroxy-17beta-methylestra-1,3,5(10)-triene-2-carboxaldehyde

HRID 343308Notes

Reaction equation

HRID 343308 reaction equation
[OH:1][C:2]1[C:19]([CH:20]=[O:21])=[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](=[CH2:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[H][H]>CCOC(C)=O.[Pd]>[OH:1][C:2]1[C:19]([CH:20]=[O:21])=[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@@H:11]([CH3:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 542724493-Hydroxy-17-methyleneestra-1,3,5(10)-triene-2-carboxaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 867527243-Hydroxy-17beta-methylestra-1,3,5(10)-triene-2-carboxaldehydeYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxy-17-methyleneestra-1,3,5(10)-triene-2-carboxaldehyde (23, 0.401 g, 1.35 mmol) in EtOAc (10 mL) was added 10% palladium on carbon (0.060 g). The reaction mixture was stirred for 4 h under the hydrogen atmosphere at room temperature. After the catalyst was filtered, the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (10:1→2:1, v/v) to afford 0.307 g of 27 (76% yield).

Workup

  1. filtrationAfter the catalyst was filtered
  2. customthe solvent was evaporated at reduced pressure
  3. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d018d1e82404440c934491624a6e2d74
Source dataset
uspto-grants-1999_01
Patent number
US05861388

Reaction notes

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