2-Methoxyphenylacetic acid → (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindolone

HRID 55426

Reaktionsgleichung

Reaktionsgleichung von HRID 55426
[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:10]2[CH:6]([CH2:7][NH:8][CH2:9]2)[C:5](=[O:11])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC>ClCCl.O.OC1C2N=NNC=2C=CC=1>[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:10]2[CH:6]([CH2:7][N:8]([C:36](=[O:37])[CH2:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][CH3:27])[CH2:9]2)[C:5](=[O:11])[CH2:4][CH2:3]1

Komponenten

7

Edukt 4

HCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67714288(3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-4-perhydroisoindolone

Produkt 1

HCID 67714177(3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindoloneAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178526939HCID 178526939, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2.8 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-4-perhydroisoindolone and 1.3 cm3 of triethylamine in 60 cm3 of anhydrous dichloromethane are added 1.55 g of (2-methoxyphenyl)acetic acid, 0.03 g of hydroxybenzotriazole hydrate and 1.96 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. After stirring for 20 hours at 20° C., the reaction mixture is washed with 100 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is recrystallized in ethyl ether and the crystals are drained and then dried under reduced pressure (2.7 kPa). 3.1 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindolone are obtained, in the form of a white solid melting at 184° C.

Aufarbeitung

  1. washthe reaction mixture is washed with 100 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue obtained
  5. customis recrystallized in ethyl ether
  6. customdried under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-7e0c0a8a08d54cafae99d5a80f6fa36a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624950

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