HCID 67714779, compound → HCID 23205563, compound

HRID 55434Notes

Reaction equation

HRID 55434 reaction equation
C(OC1C=CC=CC=1[C@H](C)C([N:18]1[CH2:26][C@@H:25]2[C@@H:20]([CH2:21][C@@H:22]([CH3:36])[CH2:23][C@:24]2(C2C=CC=CC=2OC)[OH:27])[CH2:19]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:36][CH:22]1[CH2:21][CH:20]2[CH:25]([CH2:26][NH:18][CH2:19]2)[CH:24]([OH:27])[CH2:23]1

Participants

5

Reactant 2

HCID 67714779HCID 67714779, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23205563HCID 23205563, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.85 g of (3aS,4S, 6R, 7aR)-2-[2-(S)-(2-benzoxyphenyl) propionyl]-4-(2-methoxyphenyl)-6-methyl-4-perhydroisoindolol in 12 cm3 of absolute ethanol is added 0.2 g of 20% palladium hydroxide on charcoal, and hydrogen is sparged through the reaction mixture at 40° C. for 3 hours. After returning to room temperature and flushing with argon, the mixture is filtered over fire and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized in ethanol and, after filtration and drying, 0.5 g of (3aS,4S,6R,7aR)-2-(S)-(2-hydroxyphenyl) propionyl]-4-(2-methoxtphenyl)-6-methyl-4-perhydroisoindolol is obtained, in the form of white crystals melting at 280° C.; [α]D =-26.5° (c=5.3 g/l , CHCl3).

Workup

  1. customis sparged through the reaction mixture at 40° C. for 3 hours
  2. customAfter returning to room temperature
  3. customflushing with argon
  4. filtrationthe mixture is filtered over fire
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is recrystallized in ethanol
  7. filtrationafter filtration
  8. customdrying

Sources & evidence

ORD record
ord-5d4df369df024bdf9f9c45dfab3d70b3
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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