Dibutyltin oxide → HCID 178520423, compound

Participants

Reaction Steps

To a solution of Example 32 (0.25 g, 0.56 mmol) in 10 mL of toluene were added successively trimethylsilylazide (0.30 mL, 4 equiv.) and dibutyltinoxide (0.06 g, 0.4 equiv.). The resulting mixture was stirred at reflux for two days. Tlc monitoring showed formation of a new compound (DCM:MeOH (80:20), Rf=0.35). The reaction mixture was concentrated in vacuo. The resulting yellow gum was dissolved in MeOH and concentrated in vacuo. The residue was partitioned between EtOAc (25 mL) and an aqueous saturated solution of NaHCO3 (25 mL). The organic phase was extracted with an additional portion of an aqueous saturated solution of NaHCO3 (25 mL). The combined aqueous extracts were acidified to pH=2 with HCl (1N) and then extracted with EtOAc (2×25 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to give a yellow powder that was purified via flash chromatography (SiO2, DCM:MeOH (90:10)). Recrystallization from 2-propanol:iPr2O (1:1) gave the title compound (0.19 g, 70%) as white crystals.

Provenance & Evidence