Indole-3-Acetic Acid → HCID 67736919, compound

HRID 1029915Notes

Reaction equation

HRID 1029915 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.[C:14]1([C:20]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]3[CH:24]([CH2:25][NH:26][CH2:27]3)[C:23](=[O:29])[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:30]1([C:20]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:28]3[CH:24]([CH2:25][N:26]([C:11](=[O:13])[CH2:10][C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)[CH2:27]3)[C:23](=[O:29])[CH2:22][CH2:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 802Indole-3-Acetic AcidHCID 21264544(3aRS,7aRS)-7,7-Diphenylperhydro-4-isoindolone

Product 1

HCID 67736919HCID 67736919, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-Carbonyldiimidazole (4.05 g) is added to a solution of 2-(3-indolyl)acetic acid (4.37 g) in dry dichloromethane (100 cc), cooled to +5° C. The mixture is stirred for 1 hour at +5° C. and (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone (7.3 g) is then added. The reaction mixture is stirred at 20° C. for 20 hours, then washed with distilled water (3×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 7 cm, height 40 cm), eluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume) and collecting 100 cc fractions. Fractions 6 to 11 are concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from acetonitrile (50 cc). The crystals obtained are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-(3-indolyl)acetyl]-4-perhydroisoindolone (5 g) melting at 250° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 20 hours
  3. washwashed with distilled water (3×50 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 7 cm, height 40 cm)
  8. washeluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume)
  9. customcollecting 100 cc fractions
  10. concentrationFractions 6 to 11 are concentrated to dryness under reduced pressure (2.7 kPa)
  11. customThe residue is recrystallized from acetonitrile (50 cc)
  12. customThe crystals obtained
  13. washwashed with isopropyl ether (10 cc)
  14. customdried

Sources & evidence

ORD record
ord-8318cec0b1af45c88d5d45c895a354b7
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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