反应详情

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylate (from Step 2) in THF/acetone (0.2 M, 1:1, v:v) was added N-methyl morpholine N-oxide (1.2 eq.). To the resulting suspension water was added (1 volume part), followed by a solution of osmium tetroxide in water (0.1 eq., 4% solution). The resulting solution was left stirring overnight at RT. After one night a saturated solution of sodium sulfite in water was added and the mixture was left stirring for 30 min. The solution was diluted with water and extracted with DCM (3×) and EtOAc (2×). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residual material was dissolved in DCM and precipitated with PE. The product was obtained as a greyish foam (91%).

1. waitThe resulting solution was left
2. waitthe mixture was left
3. stirringstirring for 30 min
4. extractionextracted with DCM (3×) and EtOAc (2×)
5. dry with materialThe combined organic extracts were dried over Na2SO4
6. customevaporated in vacuo
7. dissolutionThe residual material was dissolved in DCM
8. customprecipitated with PE