Piperonal → Methyl (1R,3S)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
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].[CH:17]1[C:22]([CH:23]=O)=[CH:21][C:20]2[O:25][CH2:26][O:27][C:19]=2[CH:18]=1>>[CH3:1][O:2][C:3]([C@H:4]1[NH:5][C@H:23]([C:22]2[CH:17]=[CH:18][C:19]3[O:27][CH2:26][O:25][C:20]=3[CH:21]=2)[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16]Participants
3
Procedure
The same method but starting from L-tryptophan methyl ester and piperonal gave the cis and trans isomers of the title compound.
Sources & evidence
- ORD record
- ord-3f59fba52b224816978f0db333a140d6
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06025494
Reaction notes
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