to other product (Table , entry 1). Then we change the strategy of reaction, after formation of (3Aa) we removed DCM at 50 °C under vacuum conditions. After that in same reaction vessel, we charged 10% Pd/C catalyst in different solvent under H2 atmosphere. While using toluene, diethyl ether (for second step) there was no any conversion of 3Aa by TLC (Table , entry 2 & 3). To our delight, using different alcoholic solvent in second step of the reaction gave product (4Aa). Interestingly, the formed product is not spirolactone (Confirmed by NMR and Single crystal data) as we generally expect, instead of that we end up with 5'-amino-4'-(ethoxycarbonyl)-2-oxo-2',4'-dihydrospiro-[indoline-3,3'-pyrrole]-1'-oxide i.e. multifunctionalized 3,3'-pyrrolidinyl spirooxindole (4Aa) with low yield in 12h (Table 1, entry 4-6). Unfortunately, the obtained product is not more stable in MeOH, EtOH, iPrOH for long time after 12 h it was started decomposing. Then we tried polar solvent like DMSO again we didn't observe any product formation (Table , entry 7). Observation from Table , entry 4-6 suggest that a polar alcoholic solvent is needed to proceed reaction smoothly. Gratifyingly, by using 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent in second step of reaction delivered the desired product 4Aa with 85% yield within 6h (Table , entry 8).