1,1'-Azobis(cyclohexanecarbonitrile) → 1-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]

Participants

Reaction Steps

A degassed solution of N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide (1.38 g) in benzene (200 ml) was heated to reflux under argon. Tris(trimethylsilyl)silane (1.32 ml) was added dropwise followed by 1,1′-azobis(cyclohexane carbonitrile) (110 mg). The reaction mixture was stirred at reflux for 20 hours then concentrated in vacuo. The residue was dissolved in ethyl acetate (60 ml), extracted with HC12N (3×60 ml). The aqueous layer was basified with 2N sodium hydroxide (250 ml) then extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over sodium sulfate and the solvent evaporated in vacuo to afford 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (766 mg) which was used as such for the next step.

Provenance & Evidence