HCID 72483448, compound → HCID 72483453, compound

HRID 2220570Notes

Reaction equation

HRID 2220570 reaction equation
[CH2:1]([O:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([CH:15]=[CH:16][CH3:17])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2].[H][H]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2]

Participants

5

Reactant 2

HCID 72483448HCID 72483448, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72483453HCID 72483453, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.50 g (12.7 mmol) of (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-propenyl-1,2,3,4,4a,9b-hexahydrodibenzofuran in THF are hydrogenated for 23 h in a hydrogen atmosphere with addition of 1.8 g of Pd/C. After completion of the uptake of hydrogen, the reaction solution is filtered and concentrated to dryness. The residue is filtered adsorptively (SiO2, toluene:n-heptane=1:1), and the beige solid obtained is recrystallised repeatedly from isopropanol at room temperature, giving (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-propyl-1,2,3,4,4a,9b-hexahydrodibenzofuran as colourless solid (melting point 128° C.).

Workup

  1. filtrationAfter completion of the uptake of hydrogen, the reaction solution is filtered
  2. concentrationconcentrated to dryness
  3. filtrationThe residue is filtered adsorptively (SiO2, toluene:n-heptane=1:1)
  4. customthe beige solid obtained
  5. customis recrystallised repeatedly from isopropanol at room temperature

Sources & evidence

ORD record
ord-f26a034fd7e74674916adcc3e45619ad
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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