Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:19])[CH2:17][CH:16]([CH3:18])[CH2:15][CH:14]2[CH:10]1[CH2:11][NH:12][CH2:13]2.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][C:30](O)=[O:31])=[CH:21]1>>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][C:30]([N:12]2[CH2:11][CH:10]3[CH:14]([CH2:15][CH:16]([CH3:18])[CH2:17][C:9]3([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[OH:19])[CH2:13]2)=[O:31])=[CH:21]1Participants
3
Procedure
In an identical manner to Example 1, 0.78 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-6-methyl-4 perhydroisoindolol and 0.52 g of 3-indoleacetic acid are used. After chromatography on a column of silica gel (0.060-0.200 mm, diameter 3.5 cm, height 40 cm), eluting under a pressure of 0.7 bar with a mixture of dichloromethane and methanol [94/6 by volume] and collecting 45 cm3 fractions, fractions 10 to 16 are concentrated to dryness and, after drying at 40° C. at 15 Pa, 1.0 g of (3aRS,4RS,6SR,7aSR)-2-(3-indolylacetyl)-4-(2-methoxyphenyl)-6-methyl-4-perhydroisoindolol is obtained in the form of a white solid.
Workup
- washAfter chromatography on a column of silica gel (0.060-0.200 mm, diameter 3.5 cm, height 40 cm), eluting under a pressure of 0.7 bar with a mixture of dichloromethane and methanol [94/6 by volume]
- customcollecting 45 cm3 fractions, fractions 10 to 16
- concentrationare concentrated to dryness
- customafter drying at 40° C. at 15 Pa
Sources & evidence
- ORD record
- ord-9fb5af901a2c42bb918e4887b3ed3e5a
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624950
Linked notes
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