Triethylamine → 5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

Reaction equation

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

Participants

Procedure

2 g of 5-(4-chlorophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester in 40 ml of isopropanol is hydrogenated with 200 mg of palladium on carbon (10%) and 0.9 ml of triethylamine at room temperature under normal hydrogen pressure. After filtering off of the catalyst, concentration of the filtrate and digesting of the residue with diisopropyl ether, 1.4 g of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester with a melting point of 201°-203° C. is obtained.