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Indole-3-Acetic Acid → (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-4-perhydroisoindolol

HRID 55400
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 55400
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:18])[CH2:17][CH2:16][CH2:15][CH:14]2[CH:10]1[CH2:11][NH:12][CH2:13]2.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29](O)=[O:30])=[CH:20]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:18])[CH2:17][CH2:16][CH2:15][CH:14]2[CH:10]1[CH2:11][N:12]([C:29](=[O:30])[CH2:28][C:21]1[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=1)[CH2:13]2
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Komponenten

6

Edukt 4

HCID 802Indole-3-Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67713920(3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-4-perhydroisoindolol

Produkt 1

HCID 67713989(3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-4-perhydroisoindololAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.5 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-4-perhydroisoindolol and 1.27 g of 3-indoleacetic acid in 40 cm3 of dichloromethane, cooled to 0° C., are added 0.08 g of 1-hydroxybenzotriazole and 1.4 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture is stirred for 18 hours at room temperature and the organic phase is then washed with twice 80 cm3 of water and then with 80 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 40 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (70/30 by volume) and collecting 40 cm3 fractions. Fractions 24 to 48 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 1.21 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-4-perhydroisoindolol are obtained in the form of an off-white foam.

Aufarbeitung

  1. washthe organic phase is then washed with twice 80 cm3 of water
  2. dry with materialwith 80 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 40 cm)
  5. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (70/30 by volume)
  6. customcollecting 40 cm3 fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-97a601b0df374ef6ba79e33cee97f1b6
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05624950

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