3-Hydroxybenzaldehyde → HCID 68886275, compound

HRID 41053Notes

Reaction equation

HRID 41053 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([NH2:21])([CH3:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=2)[NH:8][CH:7]=1.[OH:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.CO>C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1([CH3:20])[CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=3)[NH:8][C:7]=2[CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([OH:23])[CH:25]=2)[NH:21]1)=[O:22]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 887MethanolHCID 68853029HCID 68853029, compound

Product 1

HCID 68886275HCID 68886275, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (+/−)-2-amino-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-propionic acid methyl ester (800 mg, 2.60 mmol) and 3-hydroxybenzaldehyde (383 mg, 3.14 mmol, 1.2 equiv) in dry dichloromethane (20 ml) trifluoroacetic acid (200 μl, 2.6 mmol, 1 equiv) is added and the mixture is stirred under argon at room temperature. When TLC indicated the disappearance of the starting material (1 day), a little methanol is added to dissolve the precipitated product. Then it is diluted with CH2Cl2 (250 ml) and washed with 2 M aqueous HCl, aqueous NaHCO3 and water, dried, and concentrated. Column chromatography (dichloromethane-ethyl acetate, 7:1→5:1) of the residue gives (1RS,3SR)-1-(3-hydroxy-phenyl)-6-(2-methoxy-ethoxy)-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester (839 mg, 78%) and (1RS,3RS)-1-(3-hydroxy-phenyl)-6-(2-methoxyethoxy)-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester (152 mg, 14%).

Workup

  1. customthe disappearance of the starting material (1 day)
  2. dissolutionto dissolve the precipitated product
  3. washwashed with 2 M aqueous HCl, aqueous NaHCO3 and water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2af5d8d3ccda4d2e83d7942d7da8ac8d
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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