HCID 12798185, compound → HCID 12798192, compound

Participants

Reaction Conditions

Reaction Steps

In a three necked flask equipped with a stirrer and a thermometer is added 4'-(N-isopropyl-N-benzoylaminomethyl)-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (100 parts) and dissolved in a mixture of 1,5-diazabicyclo[5,4,0]-5-undecene (51 parts) and N,N-dimethylformamide (319 parts). After stirring for 24 hours at 85° C., the solution is cooled, diluted with ethyl acetate (300 parts) and washed thrice with water (50 parts). Aqueous washings are combined and washed with ethyl acetate (50 parts). The ethyl acetate solution and ethyl acetate washings are combined, washed with water (30 parts) and dried over anhydrous sodium sulfate (50 parts). After 1 hour, the drying reagent is filtered off and filtrate concentrated to dryness under reduced pressure. Obtained residue (83 parts) is dissolved in ethyl acetate (200 parts), stirred for 30 minutes with active charcoal (10 parts) and filtered through diatomaceous filter-bed. The filtrate concentrated under reduced pressure. The residue is triturated with a small amount of hexane to separate amorphous powder. This is collected by filtration and dried to afford 4-(N-isopropyl-N-benzoyl-3-amino-2-hydroxypropoxy)-1-p-toluenesulfonylindole (35 parts) in 41% yield.

Provenance & Evidence