Formaldehyde → 6-Benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid isopropyl ester
Reaktionsgleichung
[CH:1]([O:4][C:5](=[O:29])[CH:6]([NH2:28])[CH:7]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)[NH:13][CH:12]=1)[CH2:8][O:9][CH3:10])([CH3:3])[CH3:2].[CH2:30]=O>C1(C)C(C)=CC=CC=1>[CH:1]([O:4][C:5]([CH:6]1[CH:7]([CH2:8][O:9][CH3:10])[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)[NH:13][C:12]=2[CH2:30][NH:28]1)=[O:29])([CH3:3])[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution is prepared from 3.8 g of 2-amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester (10 mmol) in 80 ml of xylene and added dropwise to a suspension of 360 mg of paraformaldehyde in 60 ml of xylene heated for 45 minutes to 100° C. The mixture is then refluxed for 2 hours on a water trap. After concentration, the residue is chromatographed over silica gel with methylene chloride:acetone=1:1 as the eluent, yielding 2.5 g of 6-benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid isopropyl ester (65% yield as an oil); or