Isovanillin → Methyl 1,2,3,4-tetrahydro-1-(3-hydroxy4-methoxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 342400

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[OH:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=O>>[OH:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:8]3[NH:9][C:10]4[C:15]([C:7]=3[CH2:6][CH:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

Reactant 2

HCID 12127Isovanillin

HCID 77980L-Tryptophan, methyl ester

Product 1

HCID 22677823Methyl 1,2,3,4-tetrahydro-1-(3-hydroxy4-methoxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

Procedure

The same method but starting from racemic tryptophan methyl ester and 3-hydroxy4-methoxybenzaldehyde gave the title compound as a yellow solid m.p.:140°-148° C.

Sources & evidence

ORD record: ord-77404d035c56459a80fa594a341f927a
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859006

Linked notes

Loading…