Benzyl Bromide → HCID 9911651, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.228 g (0.63 mmol) of the product of Example 1 was dissolved in 0.5 mL of anhydrous THF in an oven dried 25 mL round bottom flask and was magnetically stirred at -78° C. under a nitrogen atmosphere. A solution of lithium bis(trimethylsilyl)amide (1.89 mL; 1.0M; 1.89 mmol) was slowly added and the resulting yellow solution was stirred at -78° C. for 1 hour. At this point 150 μL (1.26 mmol) of benzyl bromide was added via syringe, the dry ice-acetone bath was removed, the reaction mixture was allowed to warm to room temperature and was stirred an additional 2 hours. The mixture was then partitioned between EtOAc and 10% aqueous NaHSO4 and extracted. The organic layer was separated, washed once with water, once with saturated brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH--NH4OH (92:8:0.5). Evaporation of the purified fractions and drying in vacuo afforded 0.183 g (64%) of the title compound.

Provenance & Evidence