Vanillin → Methyl 1,2,3,4-Tetrahydro-l-(4-Hydroxy-3-Methoxyphenyl)-9H-Pyrido(3,4-b)Indole-3-Carboxylate

HRID 342401Notes

Reaction equation

HRID 342401 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:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[O:26][CH3:27]>>[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]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:20][C:19]=1[O:26][CH3:27]

Participants

3

Reactant 2

HCID 1183VanillinHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 3890051Methyl 1,2,3,4-Tetrahydro-l-(4-Hydroxy-3-Methoxyphenyl)-9H-Pyrido(3,4-b)Indole-3-Carboxylate

Procedure

The same method but starting from racemic tryptophan methyl ester and 4-hydroxy-3-methoxybenzaldehyde gave the title compound as a cream solid m.p.:195° C.

Sources & evidence

ORD record
ord-54c98a4f87e64061ac29e1c24a38b8be
Source dataset
uspto-grants-1999_01
Patent number
US05859006

Reaction notes

Loading…