2-Benzofurancarboxaldehyde → HCID 59125416, compound

HRID 1062564Notes

Reaction equation

HRID 1062564 reaction equation
O1C2C=CC=CC=2C=C1C=O.[CH3:12][O:13][C:14]([C@@H:16]1[CH2:28][C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]=2[C@H:18]([C:29]2[O:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH:33]=2)[NH:17]1)=[O:15]>>[CH3:12][O:13][C:14]([C@@H:16]1[CH2:28][C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]=2[C@H:18]([C:29]2[O:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH:33]=2)[NH:17]1)=[O:15].[CH3:12][O:13][C:14]([C@@H:16]1[CH2:28][C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]=2[C@@H:18]([C:29]2[O:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH:33]=2)[NH:17]1)=[O:15]

Participants

4

Reactant 2

HCID 613412-BenzofurancarboxaldehydeHCID 59125416HCID 59125416, compound

Product 2

HCID 59125416HCID 59125416, compoundYield 56%HCID 59125430HCID 59125430, compoundYield 20%

Procedure

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.

Workup

  1. customwere prepared by the same method
  2. additionThe crude mixture of diasteromers
  3. customwas separated by chromatography (Chiralcel OD-H column, 60% heptane, 40% ethanol)

Sources & evidence

ORD record
ord-7db35e14a0f642fa9182f798e6dffe29
Source dataset
uspto-grants-2005_11
Patent number
US06962918B2

Reaction notes

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