Indole-3-Acetic Acid → 4-(2-Methoxyphenyl)-7-methyl-4-perhydroisoindolol

HRID 55437

Reaction equation

HRID 55437 reaction equation
O[CH2:2][C:3]1(C)[CH:11]2[CH:7]([CH2:8][NH:9][CH2:10]2)[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])([OH:12])[CH2:5][CH2:4]1.N1C2C(=CC=CC=2)C(CC(O)=O)=C1>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:6]1([OH:12])[CH2:5][CH2:4][CH:3]([CH3:2])[CH:11]2[CH:7]1[CH2:8][NH:9][CH2:10]2

Participants

3

Reactant 2

HCID 802Indole-3-Acetic AcidHCID 67714238(3aRS,4RS,7SR,7aRS)-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol

Product 1

HCID 1317199994-(2-Methoxyphenyl)-7-methyl-4-perhydroisoindolol

Procedure

By working in an identical manner to Example 1, 1.5 g of (3aRS,4RS,7SR,7aRS)-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol and 0.88 g of 3-indoleacetic acid are used. After concentration, the crude residue is recrystallized in acetonitrile and, after drying at 40° C. and 15 Pa, 0.7 g of (3aRS,4RS,7SR,7aRS)-7-(hydroxymethyl)-2-(3-indolylacetyl)-4-(2-methoxyphenyl)-7-methyl-4ethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol is obtained, in the form of a white solid melting at 170-180° C. (pasty melt).

Workup

  1. concentrationAfter concentration
  2. customthe crude residue is recrystallized in acetonitrile
  3. customafter drying at 40° C.

Sources & evidence

ORD record
ord-99f1581b1fab49a69efa22f41c19a858
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Linked notes

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