反应详情

A mixture of 1 g (4.8 mmol) ethyl-6-hydroxyindole-2-carboxylate (Journal of the American Chemical Society (1967), 89(13), 3349-50), 0.81 g (6.3 mmol) 1-isopropyl-3-pyrrolidinol, 2.83 ml (11 mmol) tri-n-butyl-phosphine and 2.56 g (9.75 mmol) 1,1′azodicarbonyl-dipiperidine in 50 ml THF was stirred at room temperature for 16 h. The suspension was filtered and the filtrated evaporated to dryness. The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1. The product containing fractions were combined and evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane to afford 0.5 g of brownish crystals (MS (m/e): 317.1 (MH+, 100%)). and after evaporation of the filtrate 0.6 g of slightly impure product which was used without further purification in the consecutive step.

1. filtrationThe suspension was filtered
2. customthe filtrated evaporated to dryness
3. customThe residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1
4. additionThe product containing fractions
5. customevaporated to dryness
6. customto yield a brown oil which
7. customwas crystallized from diethyl ether and heptane