反应详情

1-Hexyl-5-hydroxy-2-methyl-1H-indole-3-acetamide (230 mg, 0.8 mmol) was dissolved in 10 mL of DMF and 26 mg (0.8 mmol) of 60% NaH/mineral oil added. The mixture was stirred for 1 hour, 0.115 mL (0.8 mmol) of ethyl 4-bromobutyrate added and stirring continued for 96 hours. The mixture was diluted with water, extracted with ethyl acetate, the ethyl acetate washed with water and dried (Na2SO4). The solution was concentrated at reduced pressure and the residue chromatographed on silica gel (eluted with 3% MeOH/methylene chloride) to give 170 mg (53% yield of [4-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester, mp, 69-71° C.

1. stirringstirring
2. waitcontinued for 96 hours
3. extractionextracted with ethyl acetate
4. washthe ethyl acetate washed with water
5. dry with materialdried (Na2SO4)
6. concentrationThe solution was concentrated at reduced pressure
7. customthe residue chromatographed on silica gel (eluted with 3% MeOH/methylene chloride)