Proton sponge → HCID 19045435, compound

Participants

Reaction Steps

To a solution of 1,4-dihydro-1'-methyl-7-methanesulfonamido-spiro[(3H)-2-benzopyran-3,4'-piperidine] (0.575 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (proton sponge) (0.6 g) in dichloroethane under nitrogen at 0° C. was added 1-chloroethyl chloroformate (0.613 ml). The mixture was stirred at reflux for 2 hours, cooled filtered through silca gel (20 g) and the product eluted with ethyl acetate. The eluate was concentrated and the residue dissolved in methanol (20 ml) and refluxed for 18 hours. The reaction was concentrated to a foam and crystallized from ethanol/hexanes yielding 0.548 g of product.

Provenance & Evidence