반응 #69331

반응 방정식

(+/−)-2-amino-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-propionic acid methyl ester

3-hydroxybenzaldehyde

methanol

→

(1RS,3RS)-1-(3-hydroxy-phenyl)-6-(2-methoxyethoxy)-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

수율 14.2%

용매

CH2Cl2

dichloromethane

반응 조건

후처리

1. 1
   기타the disappearance of the starting material (1 day)
2. 2
   workup.DISSOLUTIONto dissolve the precipitated product
3. 3
   세척washed with 2 M aqueous HCl, aqueous NaHCO3 and water
4. 4
   기타dried
5. 5
   농축concentrated

실험 절차

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%).

출처