Benzyl Bromide → tert-butyl [1'-benzyl-5-chloro-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

Participants

Reaction Steps

To a solution of tert-butyl (5-chloro-2,5′-dioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl)acetate, intermediate 32 (175.00 mg; 0.50 mmol) in dry THF (5 mL), sodium hydride (24 mg; 0.60 mmol) was added. The reaction mixture was stirred 15 minutes then benzyl bromide (71.10 μl; 0.60 mmol) was added. After stirring for 10 min, the solvent was evaporated and the residue redissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and removed in vacuo to give a residue which was purified by chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate (20 to 50%) to give the title compound was obtained (220 g, 52.1%, HPLC purity 96.7%). MS (ESI+): 441.4; MS (ESI−): 439.2

Provenance & Evidence