Dimethylformamide → Diisopropylether hexane

Participants

Reaction Steps

A mixture of (1R,4R)-5-(4-hydroxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVIII, 0.15 g, 0.48 mmol), the appropriate alkyl halide (0.97 mmol), potassium carbonate (0.13 g, 0.97 mmol) and dimethylformamide (1 ml) was shaken at about 50° C. for about 24 hours. The mixture was diluted with ethyl acetate, washed 4 times with water, dried over sodium sulfate, filtered and concentrated. Trituration of the residue from isopropyl ether-hexane afforded the corresponding (1R,4R)-5-(4-arylmethoxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXIX) as a colorless solid.

Provenance & Evidence