4-Fluorobenzaldehyde → methyl 1-(4-fluorophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate

HRID 324386

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].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>>[F: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][CH:19]=1

Participants

Reactant 2

HCID 680234-Fluorobenzaldehyde

HCID 77980L-Tryptophan, methyl ester

Product 1

HCID 4691803methyl 1-(4-fluorophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate

Procedure

The same method as employed in the preparation of intermediate 1 and 2 but starting from racemic tryptophan methyl ester and 4-fluorobenzaldehyde gave the cis isomer as white crystals m.p.: 92° C. and the trans isomer as pale yellow crystals m.p.: 183° C.

Workup

customgave the cis

Sources & evidence

ORD record: ord-b6318b0930ae49eaaa9aeea1d37f4bf0
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218400B1

Linked notes

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