2-Benzofurancarboxaldehyde → HCID 59125416, compound

Participants

Reaction Steps

Using benzofuran-2-carbaldehyde as the starting aldehyde, Intermediates 1 and 2 were prepared by the same method described below for (1R,3S)- and (1S,3S)-1-(3-methyl-benzo[b]thiophen-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediates 3 and 4). The crude mixture of diasteromers was separated by chromatography (Chiralcel OD-H column, 60% heptane, 40% ethanol) to yield 2.5 g (56%) of (1R,3S)-1-benzofuran-2-yl,2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediate 1) and 920 mg (20%) of (1S,3S)-1-benzofuran-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediate 2) as foams.

Provenance & Evidence