956141-90-5 → 5-Chloro-2,3-dihydrospiro[1H-indene-1,3′-pyrrolidine]

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-chloro-2,3-dihydrospiro[indene-1,3′-pyrrolidine]-2′,5′-dione (Prep7, 3 g, 12.7 mmol) in anhydrous THF (20 ml) at 0° C. and under a nitrogen atmosphere, BH3(CH3)2S complex in THF (1M, 50 ml) was added dropwise. The ice-bath was removed, the reaction mixture was allowed to reach room temperature and refluxed for 28 h. The mixture was then cooled to 0° C. and hydrochloric acid (2 M, 30 ml) was cautiously added monitoring gas evolution, then the ice-bath was removed and the reaction was stirred for 1 h. THF was then removed in vacuo, the residue was cooled to 0° C. DCM was added and the stirred mixture was treated with a solution of NaOH (2M) until pH=13. The mixture was extracted with additional DCM, the solvent was evaporated under vacuum to obtain the crude title compound (3 g).

Provenance & Evidence