Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate → tert-butyl 2,2-difluoro-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-quinoline]-1'-carbamate

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Reaction Steps

0.275 g of tert-butyl 4-methylene-3,4-dihydro-2H-quinoline-1-carbamate, 0.0028 g of sodium fluoride and 1.5 ml of toluene are placed in a 10 ml round-bottomed flask equipped with a magnetic stirrer and placed under an inert atmosphere. The reaction mixture is heated at reflux for 1 h. 0.449 g of methyl fluorosulfonyldifluoroacetate is subsequently added and the reaction mixture is heated at reflux for 2 h, filtered through celite and then concentrated under reduced pressure. The residue is chromatographed twice on silica gel eluted with dichloromethane. 0.23 g of tert-butyl 2,2-difluoro-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-quinoline]-1′-carbamate is obtained.

Provenance & Evidence