2,3-Dihydro-5-methoxy-6-(phenylmethoxy)-2-(phenylmethyl)-1H-isoindole → 2,3-dihydro-6-methoxy-1H-isoindol-5-ol

HRID 1684391Notes

Reaction equation

HRID 1684391 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13]C1C=CC=CC=1)[CH2:8][N:7](CC1C=CC=CC=1)[CH2:6]2>[OH-].[OH-].[Pd+2].C(O)C>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][CH2:8]2)=[CH:4][C:3]=1[OH:2]

Participants

4

Reactant 1

HCID 107363032,3-Dihydro-5-methoxy-6-(phenylmethoxy)-2-(phenylmethyl)-1H-isoindole

Product 1

HCID 102411352,3-dihydro-6-methoxy-1H-isoindol-5-olYield 87.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 35 mL of ethyl alcohol is added 0.5 g of 2,3-dihydro-5-methoxy-6-(phenylmethoxy)-2-(phenylmethyl)-1H-isoindole. The solution is warmed until everything is dissolved. The solution is cooled to room temperature and 0.13 g of 35% palladium hydroxide on carbon is added. The resulting mixture is shaken on a Parr apparatus at 50 pounds per square inch for 21 hours. The solution is filtered through a pad of diatomaceous earth and the pad washed with ethyl alcohol. The volatiles are removed to afford 0.209 g of the desired product as a tan solid.

Workup

  1. temperatureThe solution is warmed until everything
  2. dissolutionis dissolved
  3. filtrationThe solution is filtered through a pad of diatomaceous earth
  4. washthe pad washed with ethyl alcohol
  5. customThe volatiles are removed

Sources & evidence

ORD record
ord-c99e7d48541b4fd2afd7924e80e40596
Source dataset
uspto-grants-1997_06
Patent number
US05639887

Reaction notes

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