7,7-dimethyl-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindolone → (3aR*,4R*,7aR*)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindolol

HRID 55407Notes

Reaction equation

HRID 55407 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:10]2[CH:6]([CH2:7][N:8]([C:11](=[O:22])[C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH3:13])[CH2:9]2)[C:5](=[O:23])[CH2:4][CH2:3]1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Mg]Br>>[CH3:24][C:2]1([CH3:1])[C@H:10]2[C@H:6]([CH2:7][N:8]([C:11](=[O:22])[C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH3:13])[CH2:9]2)[C@:5]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])([OH:23])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 228722957,7-dimethyl-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindoloneHCID 178489560HCID 178489560, compound

Product 1

HCID 53755225(3aR*,4R*,7aR*)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindololYield 26.1%

Procedure

By working according to the experimental procedure of Example 9, from 0.78 g of 7,7-dimethyl-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindolone (mixture of (3aR,7aR) and (3aS,7aS) diastereoisomers) and 1.5 g of 2-methoxyphenylmagnesium bromide, and after purification on a column of silica gel (particle size 0.04-0.06 mm, diameter 2.8 cm, height 21 cm), 0.27 g of (3aR*,4R*,7aR*)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[2-(S)-(2-methoxyphenyl)propionyl]-4-perhydroisoindolol is obtained, in the form of a white foam.

Workup

  1. customafter purification on a column of silica gel (particle size 0.04-0.06 mm, diameter 2.8 cm, height 21 cm)

Sources & evidence

ORD record
ord-0008739af5254e98b55f5e62b26866ee
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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