반응 #69330

반응 방정식

Methanol

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

3-hydroxybenzaldehyde

trifluoroacetic acid

→

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

수율 93.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.DISSOLUTIONto dissolve the precipitated product
2. 2
   세척It is washed with saturated aqueous NaHCO3 (2×50 ml) and water (2×50 ml)
3. 3
   기타is dried
4. 4
   기타the solvent is removed under reduced pressure
5. 5
   기타The residue is purified by column chromatography (dichloromethane-ethyl acetate, 7:1→4:1)

실험 절차

A mixture of (+/−)-2-amino-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl ester (829 mg, 3 mmol), 3-hydroxybenzaldehyde (439 mg, 3.6 mmol) and trifluoroacetic acid (223 μl, 3 mmol) in dry dichloromethane (40 ml) is stirred for 6 h under argon. Methanol (2 ml) is added to dissolve the precipitated product and the mixture is diluted with dichloromethane (150 ml). It is washed with saturated aqueous NaHCO3 (2×50 ml) and water (2×50 ml), is dried, and the solvent is removed under reduced pressure. The residue is purified by column chromatography (dichloromethane-ethyl acetate, 7:1→4:1) to provide (1RS,3SR)-1-(3-hydroxy-phenyl)-6-ethoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester (1.05 g, 93%). M.p. 173-175° C. (from ethyl acetate-hexane).

출처