Potassium Carbonate → methyl 2-(5,5-dimethyl-5'-(N-(2-morpholinoethyl)-methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

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Reaction Conditions

Reaction Steps

A mixture of methyl 2-(5,5-dimethyl-5′-(methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.400 g, 1.004 mmol), 4-(2-chloroethyl)morpholine hydrochloride (0.224 g, 1.204 mmol) (prepared in an analogous manner as described in Example 17, Scheme 17, Steps 1, 2, 3, 4) and K2CO3 (0.306 g, 2.208 mmol) in DMF (8 ml) was heated at 70° C. for 3 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed several times with brine and dried over sodium sulfate; the solvent was removed and the crude was purified by chromatography on silica gel cartridge (DCM:MeOH=99:1 to 97:3) affording methyl 2-(5,5-dimethyl-5′-(N-(2-morpholinoethyl)-methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.453 g, 0.885 mmol, 88% yield, MS/ESI+ 512.1 [MH]+).

Provenance & Evidence