(S)-2-(2-Methoxyphenyl)propanoic acid → HCID 67714410, compound

HRID 55436Notes

Reaction equation

HRID 55436 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]1([OH:18])[CH2:16][C@H:15]([CH3:17])[CH2:14][C@@H:13]2[C@H:9]1[CH2:10][NH:11][CH2:12]2.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C@H:27]([CH3:31])[C:28](O)=[O:29]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]1([OH:18])[CH2:16][C@H:15]([CH3:17])[CH2:14][C@@H:13]2[C@H:9]1[CH2:10][N:11]([C:28](=[O:29])[C@H:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH3:19])[CH3:31])[CH2:12]2

Participants

3

Reactant 2

HCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acidHCID 22872289HCID 22872289, compound

Product 1

HCID 67714410HCID 67714410, compoundYield 48.5%

Procedure

By working as in Example 33, but starting with 2.5 g of (3aS,4S,6R,7aR)-4-(2-fluorophenyl)-6-methyl-4-perhydroisoindolol and 2.17 g of 2-(S)-(2-methoxyphenyl)propionic acid, and after purification on a column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 25 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume), 3.87 g of a solid are obtained, which solid is recrystallized in acetonitrile to give 2 g of (3aS,4S,6R,7aR)-4-(2-fluorophenyl)-2-[2-(S)-(2-methoxyphenyl) propionyl]-6- methyl-4-perhydroisoindolol, in the form of a white solid melting at 170° C.

Workup

  1. customafter purification on a column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 25 cm)
  2. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume), 3.87 g of a solid
  3. customare obtained
  4. customwhich solid is recrystallized in acetonitrile

Sources & evidence

ORD record
ord-6393d82c72df4a58a4a4ba5bf7cc8188
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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