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Ethyl Acetate → (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol

HRID 55429
Notes
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Reaction equation

HRID 55429 reaction equation
[OH:1][C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH:10]2[CH:6]([CH2:7][N:8]([C:11](=[O:21])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH2:9]2)[C:5](=[O:22])[CH2:4][CH2:3]1.C[Li].[Cl-].[NH4+].[C:35](OCC)(=O)C>C(OCC)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:2]1([OH:1])[CH2:3][CH2:4][C:5]([CH3:35])([OH:22])[CH:6]2[CH:10]1[CH2:9][N:8]([C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67714177(3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindoloneHCID 178418348HCID 178418348, compound

Product 1

HCID 67714344(3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol

Reagents, catalysts & solvents

1
HCID 3283Diethyl EtherSolvent

Procedure

To a suspension, cooled to -70° C. and under an argon atmosphere, of 0.5 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl ]-4-perhydroisoindolone are slowly added 4 cm3 of 1.6 M methyllithium solution in ethyl ether. After returning to room temperature and stirring for 3 hours, the reaction mixture is cooled to +5° C., followed by addition of 25 cm3 of saturated aqueous ammonium chloride solution and 20 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate and then in a mixture of ethyl acetate and methanol (90/10 by volume). After drying under reduced pressure and recrystallization in acetonitrile, 0.1 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol is obtained, in the form of white crystals melting at 180° C.

Workup

  1. customAfter returning to room temperature
  2. temperaturethe reaction mixture is cooled to +5° C.
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate
  6. additionin a mixture of ethyl acetate and methanol (90/10 by volume)
  7. dry with materialAfter drying under reduced pressure and recrystallization in acetonitrile

Sources & evidence

ORD record
ord-a0a4d743231c43d0a783e1950f3a64f0
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05624950

Reaction notes

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