Indole-3-Acetic Acid → 4-(2-Methoxyphenyl)-7-methyl-4-perhydroisoindolol
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]2Participants
3
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
- concentrationAfter concentration