Butanal → methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride

HRID 65081

Reaktionsgleichung

Reaktionsgleichung von HRID 65081
[ClH:1].[CH3:2][O:3][C:4](=[O:17])[CH:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[CH:18](=O)[CH2:19][CH2:20][CH3:21]>CO>[ClH:1].[CH2:19]([C@H:18]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH2:7][C@@H:5]([C:4]([O:3][CH3:2])=[O:17])[NH:6]1)[CH2:20][CH3:21]

Komponenten

4

Edukt 2

HCID 261ButanalHCID 2827264methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Produkt 1

HCID 86741021methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochlorideAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of DL-tryptophan methyl ester hydrochloride (33 g), n-butyraldehyde (21.0 g) and methanol (450 ml) is refluxed for 48 hours. After the reaction, the reaction mixture is concentrated to about 1/3 in volume and allowed to stand. The precipitated crystals are collected by filtration and recrystallized from methanol to give methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride (15.4 g, 38.4%) as colorless prisms, m.p. 205°-207° C.

Aufarbeitung

  1. temperatureis refluxed for 48 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture is concentrated to about 1/3 in volume
  4. filtrationThe precipitated crystals are collected by filtration
  5. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-867da906609240f199ae86d2289c2afe
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612317

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