HCID 68710644, compound → HCID 68709571, compound

HRID 2376431Notes

Reaction equation

HRID 2376431 reaction equation
O[CH:2]([C:4]1[C:12]2[O:11][CH2:10][C@H:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:8]=2[C:7]([CH3:22])=[C:6]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]=1[CH3:31])[CH3:3]>[Pd].C(O)C>[CH2:2]([C:4]1[C:12]2[O:11][CH2:10][C@H:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:15][CH:14]=3)[C:8]=2[C:7]([CH3:22])=[C:6]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:5]=1[CH3:31])[CH3:3]

Participants

4

Reactant 1

HCID 68710644HCID 68710644, compound

Product 1

HCID 68709571HCID 68709571, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (+)-N-((3R)-7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (746 mg, 1.77 mmol) obtained in Examples 40 and 41, and 10% palladium on carbon (water content: 50%, 75 mg) in ethanol (8 mL) was refluxed with heating for 2 hours. The catalyst was removed and the reaction solution was concentrated under reduced pressure. The obtained residue was recrystallized from THF-hexane to obtain 589 mg (yield: 96%) of the title compound. Melting point: 156-157° C. [α]D20=+50.7° (c=0.46, chloroform).

Workup

  1. temperaturewith heating for 2 hours
  2. customThe catalyst was removed
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe obtained residue was recrystallized from THF-hexane

Sources & evidence

ORD record
ord-133b436e3fe34241be619167306cac83
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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