HCID 68707809, compound → HCID 68710539, compound

HRID 2376432Notes

Reaction equation

HRID 2376432 reaction equation
O[CH:2]([C:5]1[C:13]2[O:12][CH2:11][C@H:10]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[C:9]=2[C:8]([CH3:23])=[C:7]([NH:24][C:25](=[O:31])[CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:6]=1[CH3:32])[CH2:3][CH3:4]>[Pd].C(O)(=O)C>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([C@@H:10]2[C:9]3[C:8]([CH3:23])=[C:7]([NH:24][C:25](=[O:31])[CH2:26][C:27]([CH3:28])([CH3:30])[CH3:29])[C:6]([CH3:32])=[C:5]([CH2:2][CH2:3][CH3:4])[C:13]=3[O:12][CH2:11]2)=[CH:15][CH:16]=1)([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 68707809HCID 68707809, compound

Product 1

HCID 68710539HCID 68710539, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of a diastereo mixture of (+)-N-((3R)-7-(1-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (620 mg, 1.42 mmol) obtained in Examples 43 and 44, and 10% palladium on carbon (water content: 50%, 62 mg) in acetic acid (3 mL) was reacted at 80° C. for 2 hours. The catalyst was removed, water was added to the reaction solution, and the product was extracted with ethyl acetate. The organic layer was washed with water, an aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate-hexane to obtain 423 mg (yield: 71%) of the title compound. Melting point: 184-185° C. [α]D20=+41.6° (c=0.51, chloroform).

Workup

  1. customwas reacted at 80° C. for 2 hours
  2. customThe catalyst was removed
  3. additionwater was added to the reaction solution
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialan aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b8232fa2b31a496480ac959915d8721f
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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