Triethylamine → HCID 53662264, Verbindung

HRID 1720323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720323
[CH2:1]([O:3][C:4]([CH:6]1[CH:18]([CH2:19][O:20][CH3:21])[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.C(OCl)(C)(C)C>C1(C)C=CC=CC=1.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 545410741,2,3,4-Tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Produkt 1

HCID 53662264HCID 53662264, VerbindungAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1 g (0.0024 mol) of 1,2,3,4-tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is mixed in a mixture of 20 ml of toluene and 7 ml of dichloromethane at -15° C. with 1.2 ml of triethylamine. Then 0.9 ml (0.0074 mol) of tert.butylhypochlorite, dissolved in 12 ml of dichloromethane, is instilled. The reaction mixture is stirred at room temperature for two more hours. The evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane and yields 0.33 g (33% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, melting point 182°-184° C. (from ethanol).

Aufarbeitung

  1. customThe evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3332e4d99bd34a488c8ca6e37219bbb0
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506234

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