Isopropyl iodide → HCID 23459827, compound

Participants

Reaction Conditions

Reaction Steps

THF, 20 ml is placed under N2, treated with 1.54 ml diisopropylamine and cooled to -78° C. A solution of n-butyl lithium (1.97 M in hexane; 5.6 ml) is added dropwise over 5 min. The reaction mixture is stirred at -78° C. for 10 min. and then treated with 8-oxo-2,2,6-trimethyl-3-oxa-1-azabicyclo[4.2.0]octane (0.0079 mmole) ml THF added dropwise over 5 min. After another 10 min. hexamethylphosphoramide 1.97 ml is added. The mixture is stirred another 10 min., then treated with 2 ml of isopropyl iodide. The reaction mixture is stirred at -78° C. for 15 min. and allowed to warm to 25° C. and stirred for 15 min. The reaction mixture is diluted with EtOAc, washed once with pH 7 phosphate buffer then dried and evaporated. The residue is chromatographed on silica gel using 25% EtOAc/C6H6 as eluant to give 8-oxo-2,2,6-trimethyl-7-isopropyl-3-oxa-1-azabicyclo[4.2.0]-octane.

Provenance & Evidence