Bromomethyl pivalate → Pivaloyloxymethyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

Participants

Reaction Steps

To a stirring suspension of sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (20 mg) in anhydrous hexamethylphosphoramide (0.5 ml) is added bromomethyl pivalate (35 mg). The resulting mixture is stirred at room temperature for 2 hrs, then diluted with benzene (5 ml) and washed thoroughly with H2O (5×2 ml) and brine. The benzene solution is dried with MgSO4, filtered, and concentrated under reduced pressure. Preparative tlc of the residue on a silica gel GF plate provides pivaloyloxymethyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate.

Provenance & Evidence