HCID 19363419, compound → HCID 19363480, compound

HRID 850497Notes

Reaction equation

HRID 850497 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:32][CH3:33])[C:23]=3[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:18]2=[O:34])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:32][CH3:33])[C:23]=3[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:18]2=[O:34])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 19363419HCID 19363419, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363480HCID 19363480, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(4-Benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one (125.9 mg, 0.274 mmol, 1.0 eq) was dissolved in ethyl acetate (10 ml), and 100% palladium-carbon catalyst (80 mg, water content 50%) was added. The mixture was stirred in a stream of hydrogen for 3 hours. After the completion of the reaction, the mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-[2-(4-hydroxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one (5 mg, 74.1%) as colorless crystals.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-7a341e2a4d924ad5b8d280d4787eb47f
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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