3-Furaldehyde → Methyl 1,2,3,4-Tetrahydro-1-(3-Furyl)-9H-Pyrido(3,4-b) Indole-3-Carboxylate

HRID 377447Notes

Reaction equation

HRID 377447 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].[O:17]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18]1>>[O:17]1[CH:21]=[CH:20][C:19]([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:18]1

Participants

3

Reactant 2

HCID 103513-FuraldehydeHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 22677851Methyl 1,2,3,4-Tetrahydro-1-(3-Furyl)-9H-Pyrido(3,4-b) Indole-3-Carboxylate

Procedure

The same method but starting from racemic tryptophan methyl ester and 3-furaldehyde gave the title compound as a yellow solid m.p.:130° C.

Sources & evidence

ORD record
ord-f78e474408574764bd8c66cfe4c55386
Source dataset
uspto-grants-2000_02
Patent number
US06025494

Reaction notes

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