p-(Trifluoromethoxy)benzaldehyde → Ethyl 1,2,3,4-tetrahydro-1-(4-trifluoromethoxyphenyl)-9h-pyrido(3,4-b)indole-3-carboxylate

HRID 377454

Reaction equation

HRID 377454 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6])[CH3:2].[F:18][C:19]([F:30])([F:29])[O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>>[F:18][C:19]([F:29])([F:30])[O:20][C:21]1[CH:22]=[CH:23][C:24]([CH:25]2[C:9]3[NH:10][C:11]4[C:16]([C:8]=3[CH2:7][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:17])[NH:6]2)=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 81996L-Tryptophan, ethyl ester

Product 1

HCID 22619830Ethyl 1,2,3,4-tetrahydro-1-(4-trifluoromethoxyphenyl)-9h-pyrido(3,4-b)indole-3-carboxylate

Procedure

The same method but starting from racemic tryptophan ethyl ester and 4-trifluoromethoxybenzaldehyde gave cis and trans isomers of the title compound.

Sources & evidence

ORD record
ord-42975b34b0d948b59f8e8ce9116df3aa
Source dataset
uspto-grants-2000_02
Patent number
US06025494

Linked notes

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